reaction_id stringlengths 36 36 | reaction_cxsmiles stringlengths 93 6.14k | reactants stringlengths 2 2.48k | reactants_names stringlengths 1 2.68k | reactants_amounts stringlengths 3 323 | reactants_units stringlengths 1 323 | solvents stringlengths 1 267 ⌀ | solvents_names stringlengths 1 221 ⌀ | solvents_amounts stringlengths 3 82 ⌀ | solvents_units stringclasses 744
values | catalysts stringlengths 1 683 ⌀ | catalysts_names stringlengths 1 365 ⌀ | catalysts_amounts stringlengths 3 62 ⌀ | catalysts_units stringclasses 108
values | reagents float64 | reagents_names float64 | reagents_amounts float64 | reagents_units float64 | temperature_celsius stringclasses 646
values | reaction_time_hours float64 0 2.16k ⌀ | product stringlengths 1 889 ⌀ | product_name stringlengths 1 381 | product_amount float64 0 1.83M ⌀ | product_unit stringclasses 3
values | product_yield float64 0 90,205,160,000B ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord-89aff4b1c18042e4bbb1f88ebba96f86 | S(Cl)([Cl:3])=O.[CH2:5]([O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>>[CH2:5]([O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([Cl:3])=[O:19])=[CH:16][CH:15]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12] | S(=O)(Cl)Cl.C(CCCCCCC)OC1=CC=C(C(=O)O)C=C1.C(CCCCCCC)OC1=CC=C(C(=O)O)C=C1 | thionyl chloride;p-octyloxybenzoic acid;( 1 ) | 0.0;10.0;0.0 | mol;g;mol | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C(CCCCCCC)OC1=CC=C(C(=O)Cl)C=C1 | 4-octyloxybenzoic acid chloride | null | null | null |
ord-c218088b16c541088a933a7606f68c4c | [OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[C:11](Cl)(=[O:21])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].N1C=CC=CC=1>O>[C:11]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)(=[O:21])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19... | OC1=CC=C(C(=O)O)C=C1.C(CCCCCCCCC)(=O)Cl.N1=CC=CC=C1 | p-hydroxybenzoic acid;decanoic acid chloride;pyridine | 0.0;15.0;7.2 | mol;g;g | O | water | 0.0 | mol | null | null | null | null | null | null | null | null | null | 24 | C(CCCCCCCCC)(=O)OC1=CC=C(C(=O)O)C=C1 | p-decanoyloxybenzoic acid | null | null | null |
ord-d965967cbe69411f9fd760ac1f990dfb | F[C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH:12][C:13]1C=CC(C(O)=O)=C[CH:14]=1.C(OC1C=CC(C(Cl)=O)=CC=1)(=O)CCCCCCCCC>>[C:13]([O:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[CH:2][CH:10]=1)(=[O:12])[CH3:14] | OC1=CC=C(C(=O)O)C=C1.FC1=C(C(=O)O)C=CC(=C1)O.C(CCCCCCCCC)(=O)OC1=CC=C(C(=O)Cl)C=C1.OC1=CC=C(C(=O)O)C=C1 | p-hydroxybenzoic acid;2-fluoro-4-hydroxybenzoic acid;( 2 );p-hydroxybenzoic acid | 0.0;0.0;0.0;0.0 | mol;mol;mol;mol | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C(C)(=O)OC1=CC=C(C(=O)O)C=C1 | p-Acetoxybenzoic acid | null | null | null |
ord-e8642ae0ecb248809067cd131fde0eed | [NH2:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[C:18]1([N:24]=[C:25]=[S:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[C:18]1([NH:24][C:25]([NH:1][C:2]2[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([NH:15][C:25](=[S:26])[N... | NC1=CC=C(C(=O)NC2=CC=C(C=C2)N)C=C1.C1(=CC=CC=C1)N=C=S | 4,4'-Diaminobenzanilide;phenylisothiocyanate | 0.658;0.676 | g;g | CC(=O)C | acetone | 20.0 | mL | null | null | null | null | null | null | null | null | 55.0 | 0.1667 | C1(=CC=CC=C1)NC(=S)NC1=CC=C(C(=O)NC2=CC=C(C=C2)NC(NC2=CC=CC=C2)=S)C=C1 | colorless crystal | 0.9 | g | 72.3 |
ord-83e2d9b7b08846c09e3e4e23f2dc9784 | [NH2:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:18]([N:25]=[C:26]=[S:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[CH2:18]([NH:25][C:26]([NH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:26](=... | NC1=CC=C(C(=O)NC2=CC=C(C=C2)N)C=C1.C(C1=CC=CC=C1)N=C=S | 4,4'-Diaminobenzanilide;benzylisothiocyanate | 0.568;0.746 | g;g | CC(=O)C | acetone | 20.0 | mL | null | null | null | null | null | null | null | null | 55.0 | 0.1667 | C(C1=CC=CC=C1)NC(=S)NC1=CC=C(C(=O)NC2=CC=C(C=C2)NC(NCC2=CC=CC=C2)=S)C=C1 | colorless crystal | 0.57 | g | 43.4 |
ord-96af32b871984951b1483d8522037b06 | [CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([NH2:8])[CH:2]=1.[CH2:9]([N:16]=[C:17]=[S:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(OCC)(=O)C>[CH2:9]([NH:16][C:17]([NH:7][C:6]1[CH:5]=[CH:4][C:3]([NH:8][C:17](=[S:18])[NH:16][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:2][CH:1]=1)=[S:18])[C:10]1[CH:15]=... | C1=CC(=CC=C1N)N.C(C1=CC=CC=C1)N=C=S | p-Phenylenediamine;benzylisothiocyanate | 2.707;7.461 | g;g | C(C)(=O)OCC | ethyl acetate | 20.0 | mL | null | null | null | null | null | null | null | null | 80.0 | 0.5 | C(C1=CC=CC=C1)NC(=S)NC1=CC=C(C=C1)NC(NCC1=CC=CC=C1)=S | colorless crystal | 6.26 | g | 61.6 |
ord-86468e176b4c448b95c93ea7f5a809d2 | [CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([CH3:9])=[CH:4][C:3]=1[NH2:10].[C:11]([N:19]=[C:20]=[S:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(OCC)(=O)C>[C:11]([NH:19][C:20]([NH:8][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([NH:10][C:20](=[S:21])[NH:19][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[... | CC1=C(C=C(C(=C1)N)C)N.C(C1=CC=CC=C1)(=O)N=C=S | 2,5-Dimethyl-p-phenylenediamine;benzoylisothiocyanate | 0.34;0.816 | g;g | C(C)(=O)OCC | ethyl acetate | 30.0 | mL | null | null | null | null | null | null | null | null | ambient | 0.1667 | C(C1=CC=CC=C1)(=O)NC(=S)NC1=C(C=C(C(=C1)C)NC(NC(C1=CC=CC=C1)=O)=S)C | colorless crystal | 1.14 | g | 98.7 |
ord-d421bcbbd72f4cb18c2bcf8464545117 | [C:1]1([NH2:12])[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([NH2:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:13]([N:20]=[C:21]=[S:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(OCC)(=O)C>[CH2:13]([NH:20][C:21]([NH:12][C:1]1[C:10]2[C:5](=[C:6]([NH:11][C:21](=[S:22])[NH:20][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:... | C1(=CC=CC=2C(=CC=CC12)N)N.C(C1=CC=CC=C1)N=C=S | 1,5-Naphthalenediamine;benzylisothiocyanate | 0.791;1.492 | g;g | C(C)(=O)OCC | ethyl acetate | 20.0 | mL | null | null | null | null | null | null | null | null | 80.0 | 0.5 | C(C1=CC=CC=C1)NC(=S)NC1=CC=CC2=C(C=CC=C12)NC(NCC1=CC=CC=C1)=S | colorless crystal | 0.7 | g | 30.7 |
ord-178874a666824f65bd0ae92352c272a1 | [OH2:1].[OH:2][CH2:3][CH:4]([CH2:6][OH:7])[OH:5]>>[OH:2][CH2:3][C@@H:4]([C@H:6]([C@@H:6]([C@@H:4]([CH2:3][OH:2])[OH:5])[OH:1])[OH:7])[OH:5] | OCC(O)CO.O.O | glycerine;water;water | 0.0;0.0;0.0 | mol;mol;mol | null | null | null | null | null | null | null | null | null | null | null | null | null | null | OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO | sorbitol | null | null | null |
ord-c078782347f44c58bb85cd3aadab3128 | [Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:17]O>>[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([O:9][CH3:17])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1 | ClC1=CC=C(C(C(=O)O)=C1)O.S(O)(O)(=O)=O.CO | 5-Chlorosalicylic acid;sulfuric acid;methanol | 0.0;0.0;0.0 | mol;mol;mol | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC1=CC=C(C(C(=O)OC)=C1)O | methyl 5-chlorosalicylate | null | null | null |
ord-e00a6267a6b742de87d3f8d8a6c2a5b7 | [C:1]([O-:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([O-:11])=[O:10])([C:5]([O-:7])=[O:6])[OH:4].[CH3:14][C:15]([CH3:17])=[O:16]>CO>[C:1]([O-:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([O-:11])=[O:10])([C:5]([O-:7])=[O:6])[OH:4].[CH3:14][C:15]([CH3:17])=[O:16].[CH3:3][OH:4] |f:3.4.5| | C(CC(O)(C(=O)[O-])CC(=O)[O-])(=O)[O-].CC(=O)C | Citrate;Acetone | 18.0;27.0 | mL;mL | CO | methanol | 5.0 | mL | null | null | null | null | null | null | null | null | null | null | C(CC(O)(C(=O)[O-])CC(=O)[O-])(=O)[O-].CC(=O)C.CO | Citrate Acetone MeOH | null | null | null |
ord-e1ac06e7bdc449a283a63a6a8683ed03 | [C:1]([O-:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([O-:11])=[O:10])([C:5]([O-:7])=[O:6])[OH:4].[CH3:14][C:15]([CH3:17])=[O:16]>CO>[C:1]([O-:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([O-:11])=[O:10])([C:5]([O-:7])=[O:6])[OH:4].[CH3:14][C:15]([CH3:17])=[O:16].[CH3:3][OH:4] |f:3.4.5| | C(CC(O)(C(=O)[O-])CC(=O)[O-])(=O)[O-].CC(=O)C | Citrate;Acetone | 18.0;27.0 | mL;mL | CO | methanol | 5.0 | mL | null | null | null | null | null | null | null | null | null | null | C(CC(O)(C(=O)[O-])CC(=O)[O-])(=O)[O-].CC(=O)C.CO | Citrate Acetone MeOH | null | null | null |
ord-0b3cb71fbde54da5a7c439131d7d2319 | [CH2:1]([NH:3][CH2:4][CH2:5][CH2:6][O:7][CH3:8])[CH3:2].C(O)(=O)C.[N:13]#[C:14][NH2:15].C([O-])(=O)C>>[CH3:8][O:7][CH2:6][CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[C:14]([NH2:15])=[NH:13] | C(C)NCCCOC.C(C)(=O)O.C(C)(=O)[O-].N#CN | N-ethyl-3-methoxypropylamine;acetic acid;acetate;cyanamide | 3.0;1.54;0.0;1.08 | g;g;mol;g | null | two | 50.0 | mL | null | null | null | null | null | null | null | null | 90.0 | null | COCCCN(C(=N)N)CC | title compound | 2.8 | g | 50 |
ord-b22e751eea1540b88d656fbdc64a0e99 | [CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][NH2:8].C(O)(=O)C.[N:13]#[C:14][NH2:15].C([O-])(=O)C>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][NH:8][C:14]([NH2:15])=[NH:13] | COCCOCCN.C(C)(=O)O.C(C)(=O)[O-].N#CN | 2-(2-methoxyethoxy)ethylamine;acetic acid;acetate;cyanamide | 5.96;3.0;0.0;3.1 | g;g;mol;g | null | two | 30.0 | mL | null | null | null | null | null | null | null | null | 90.0 | null | COCCOCCNC(=N)N | title compound | 3.15 | g | 28.4 |
ord-64d5f5dd2f664288acccc0452c5aa2a9 | [C:1]([O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH2:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[N:20]#[C:21][NH2:22].C([O-])(=O)C>>[C:1]([O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:21]([NH2:22])=[NH:20])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | C(C1=CC=CC=C1)(=O)OCCOCCN.C(C)(=O)O.C(C)(=O)[O-].N#CN | 2-(2-aminoethoxy)ethyl benzoate;acetic acid;acetate;cyanamide | 2.14;0.624;0.0;0.68 | g;g;mol;g | null | two | 50.0 | mL | null | null | null | null | null | null | null | null | 90.0 | null | C(C1=CC=CC=C1)(=O)OCCOCCNC(=N)N | title compound | 1.97 | g | 62.1 |
ord-84fae49193d148f395e8e28f50d554ab | C(O)(=O)C[CH2:3][C:4]([OH:6])=[O:5].O[CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:16]([NH2:18])=[NH:17].C(OC(=O)C)(=O)C.C([O-])(=O)C>C(N(CC)CC)C>[C:4]([O:6][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:16]([NH2:18])=[NH:17])(=[O:5])[CH3:3] |f:0.1| | .C(CCC(=O)O)(=O)O.OCCOCCNC(=N)N..C(C)(=O)[O-].C(C)(=O)OC(C)=O | two;2-(2-hydroxyethoxy)ethylguanidine succinate;4-N,N-dimethylaminopyridine;acetate;acetic anhydride | 50.0;2.06;0.000122;0.0;1.02 | mL;g;g;mol;g | C(C)N(CC)CC | triethylamine | 8.0 | mL | null | null | null | null | null | null | null | null | ambient | 1 | C(C)(=O)OCCOCCNC(=N)N | title compound | 1 | g | 40 |
ord-a6fad661b27341e199b0050914752841 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1(C)C=CC=CC=1>CC1C=CC(C)=CC=1>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:11][CH2:12][CH2:7][CH2:8][CH2:9][CH3:10] | CCCCCC.C1=CC=CC=C1.C1(=CC=CC=C1)C | n-hexane;benzene;toluene | 0.0;0.0;0.0 | mol;mol;mol | CC=1C=CC(=CC1)C | p-xylene | 0.0 | mol | null | null | null | null | null | null | null | null | null | null | CCCCCCCCCCCC | dodecane | null | null | null |
ord-ec57be9eb3044d5884323695460dbccf | [CH2:1]([C@H:3]([NH:10][C:11](=[O:49])[C@@H:12]([C@H:39]([CH3:48])[O:40]CC1C=CC=CC=1)[NH:13][C:14](=[O:38])[C@H:15]([CH:27](CC1C=CC=CC=1)[C:28](=[O:30])[OH:29])[NH:16]C(OCC1C=CC=CC=1)=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].C(O)(=O)C>CO.[Pd].[C]>[CH2:1]([C@H:3]([NH:10][C:11](=[O:49])[C@@H:12]([C@H:39]([CH3:4... | C(C)[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C(O)=O)CC1=CC=CC=C1)=O)[C@@H](OCC1=CC=CC=C1)C)=O.C(C)(=O)O | N-benzyloxycarbonyl-β-benzyl-L-aspartyl-O-benzyl-D-threonine (S)-α-ethylbenzylamide;acetic acid | 5.3;1.0 | g;mL | CO | methanol | 150.0 | mL | [Pd].[C] | Pd carbon | 3.0 | g | null | null | null | null | null | 8 | C(C)[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](N)CC(O)=O)=O)[C@@H](O)C)=O | α-L-aspartyl-D-threonine (S)-α-ethylbenzylamide | 1.6 | g | 57.5 |
ord-a473542e2c91474d920bd8a0505e632c | [CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([NH:26][C@@H:27]([C:32](O)=[O:33])[C@@H:28]([CH2:30][CH3:31])[CH3:29])=[O:25])[CH:13]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:14](=[O:16])[OH:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:35]([C@H:37]([NH2:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][... | C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C(O)=O)CC1=CC=CC=C1)C(=O)N[C@H]([C@H](C)CC)C(=O)O.C(C)[C@@H](C1=CC=CC=C1)N.O.C=1C=CC2=C(C1)N=NN2O | N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-isoleucine;(S)-α-ethylbenzylamine;water;HOBt | 6.69;2.04;2.73;1.92 | g;g;g;g | C(Cl)Cl | methylene chloride | 200.0 | mL | null | null | null | null | null | null | null | null | null | 1 | C(C)[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C(O)=O)CC1=CC=CC=C1)=O)[C@H](C)CC)=O | N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-isoleucine (S)-α-ethylbenzylamide | 2.81 | g | 33.1 |
ord-b4a1a9f06c874053b3ad0f85aaa15884 | [CH2:1]([C@H:3]([NH:10][C:11](=[O:43])[C@@H:12]([C@@H:39]([CH2:41][CH3:42])[CH3:40])[NH:13][C:14](=[O:38])[C@H:15]([CH:27](CC1C=CC=CC=1)[C:28](=[O:30])[OH:29])[NH:16]C(OCC1C=CC=CC=1)=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2]>CO.O.[Pd].[C]>[CH2:1]([C@H:3]([NH:10][C:11](=[O:43])[C@@H:12]([C@@H:39]([CH2:41][CH3:4... | C(C)[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C(O)=O)CC1=CC=CC=C1)=O)[C@H](C)CC)=O | N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-isoleucine (S)-α-ethylbenzylamide | 2.81 | g | CO.O | methanol;water | 150.0;50.0 | mL;mL | [Pd].[C] | Pd carbon | 2.0 | g | null | null | null | null | null | 5 | C(C)[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](N)CC(O)=O)=O)[C@H](C)CC)=O | α-L-aspartyl-D-isoleucine (S)-α-ethylbenzylamide | 1.22 | g | 72.3 |
ord-39d7a85f6c0943d29b102f7ee592196e | Cl.O1CCOCC1.[CH2:8]([C@H:10]([NH:17][C:18](=[O:32])[C:19]([CH2:30][CH3:31])([CH2:28][CH3:29])[NH:20][C:21]([O:23]C(C)(C)C)=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:9].C(N(CC)CC)C.C([CH:47]([C:63]([O-:65])=[O:64])[C@@H:48](C([O-])=O)[NH:49]C(OCC1C=CC=CC=1)=O)C1C=CC=CC=1.O.C1C=CC2N(O)N=NC=2C=1>>[CH2:8]([C@H:... | O.C=1C=CC2=C(C1)N=NN2O.Cl.O1CCOCC1.C(C)[C@@H](C1=CC=CC=C1)NC(C(NC(=O)OC(C)(C)C)(CC)CC)=O.C(C)N(CC)CC.C(C1=CC=CC=C1)C([C@H](NC(=O)OCC1=CC=CC=C1)C(=O)[O-])C(=O)[O-] | water;HOBt;HCl dioxane;N-t-butoxycarbonyl-α,α-diethylglycine (S)-α-ethylbenzylamide;triethylamine;β-benzyl-N-benzyloxycarbonyl-L-aspartate | 0.79;0.51;0.0;1.31;0.55;1.48 | g;g;mol;g;mL;g | null | null | null | null | null | null | null | null | null | null | null | null | ambient | 1 | C(C)[C@@H](C1=CC=CC=C1)NC(C(NC([C@@H](N)CC(O)=O)=O)(CC)CC)=O | α-L-aspartyl-α,α-diethylglycine (S)-α-ethylbenzylamide | 0.4 | g | 29.3 |
ord-a2a351b69552484f9b0780b4d2a5b2e4 | Cl.[O:2]1[CH2:7][CH2:6]OCC1.[CH2:8]([C@H:10]([NH:17][C:18](=[O:31])[C:19]([CH3:30])([CH2:28][CH3:29])[NH:20][C:21]([O:23]C(C)(C)C)=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:9].C([N:34]([CH2:37]C)CC)C.[OH2:39]>>[CH2:8]([C@H:10]([NH:17][C:18](=[O:31])[C:19]([CH3:30])([CH2:28][CH3:29])[NH:20][C:21](=[O:23])[C@... | Cl.O1CCOCC1..C(C)[C@@H](C1=CC=CC=C1)NC(C(NC(=O)OC(C)(C)C)(CC)C)=O.O.C(C)N(CC)CC. | HCl dioxane;0.66;N-t-butoxycarbonyl-DL-isovaline (S)-α-ethylbenzylamide;water;triethylamine;β-benzyl N-benzyloxycarbonyl-L-aspartate | 0.0;0.00197;0.0;0.34;0.24;0.63 | mol;mol;mol;g;mL;g | null | null | null | null | null | null | null | null | null | null | null | null | ambient | 1 | C(C)[C@@H](C1=CC=CC=C1)NC(C(NC([C@@H](N)CC(O)=O)=O)(CC)C)=O | α-L-aspartyl-DL-isovaline (S)-α-ethylbenzylamide | 0.21 | g | null |
ord-3d062dc2d8ab4e1391656e4f536498a8 | [ClH:1].O1CCOCC1.C(OC([NH:15][C@@H:16]([CH2:23][O:24][CH3:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O)(C)(C)C>>[ClH:1].[CH3:25][O:24][CH2:23][C@H:16]([NH2:15])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1 |f:0.1,3.4| | Cl.O1CCOCC1.C(C)(C)(C)OC(=O)N[C@H](C1=CC=CC=C1)COC | HCl dioxane;N-t-butoxycarbonyl-(R)-α-methoxymethylbenzylamine | 0.0;4.02 | mol;g | null | null | null | null | null | null | null | null | null | null | null | null | ambient | 1 | Cl.COC[C@@H](C1=CC=CC=C1)N | (R)-α-methoxymethylbenzylamine hydrochloride | null | null | null |
ord-1b033c485fa54b2cb55a6e97a581a99c | [CH3:1][O:2][CH2:3][C@H:4]([NH:11][C:12](=[O:43])[C@@H:13]([CH:40]([CH3:42])[CH3:41])[NH:14][C:15](=[O:39])[C@H:16]([CH:28](CC1C=CC=CC=1)[C:29](=[O:31])[OH:30])[NH:17]C(OCC1C=CC=CC=1)=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CO.O.[Pd].[C]>[CH3:1][O:2][CH2:3][C@H:4]([NH:11][C:12](=[O:43])[C@@H:13]([CH:40]([CH3:41])[C... | COC[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C(O)=O)CC1=CC=CC=C1)=O)C(C)C)=O | N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-valine (R)-α-methoxymethylbenzylamide | 6.2 | g | CO.O | methanol;water | 200.0;50.0 | mL;mL | [Pd].[C] | Pd carbon | 1.5 | g | null | null | null | null | 40.0 | null | COC[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](N)CC(O)=O)=O)C(C)C)=O | α-L-aspartyl-D-valine (R)-α-methoxymethylbenzylamide | 2.69 | g | 70.1 |
ord-ae03dc6af35144969588f144b56bba80 | [ClH:1].O1CCOCC1.C(OC([NH:15][C@@H:16]([CH2:23][O:24][CH2:25][CH3:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O)(C)(C)C>>[ClH:1].[CH2:25]([O:24][CH2:23][C@H:16]([NH2:15])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:26] |f:0.1,3.4| | Cl.O1CCOCC1.C(C)(C)(C)OC(=O)N[C@H](C1=CC=CC=C1)COCC | HCl dioxane;N-t-butoxycarbonyl-(R)-α-ethoxymethylbenzylamine | 0.0;0.66 | mol;g | null | null | null | null | null | null | null | null | null | null | null | null | ambient | 1 | Cl.C(C)OC[C@@H](C1=CC=CC=C1)N | (R)-α-ethoxymethylbenzylamine hydrochloride | null | null | null |
ord-29bd294101a04d54b49813c6be393808 | [CH2:1]([O:3][CH2:4][C@H:5]([NH:12][C:13](=[O:44])[C@@H:14]([CH:41]([CH3:43])[CH3:42])[NH:15][C:16](=[O:40])[C@H:17]([CH:29](CC1C=CC=CC=1)[C:30](=[O:32])[OH:31])[NH:18]C(OCC1C=CC=CC=1)=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:2]>CO.O.[Pd].[C]>[CH2:1]([O:3][CH2:4][C@H:5]([NH:12][C:13](=[O:44])[C@@H:14]([CH:41](... | C(C)OC[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C(O)=O)CC1=CC=CC=C1)=O)C(C)C)=O | N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-valine (R)-α-ethoxymethylbenzylamide | 1.2 | g | CO.O.O | methanol;water;water | 50.0;10.0;40.0 | mL;mL;mL | [Pd].[C] | Pd carbon | 0.3 | g | null | null | null | null | 40.0 | null | C(C)OC[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](N)CC(O)=O)=O)C(C)C)=O | α-L-aspartyl-D-valine (R)-α-ethoxymethylbenzylamide | 0.38 | g | 50.3 |
ord-f6a778234f084513ae50b4ca3b6875a0 | C(OC([NH:11][C@H:12]([C:24]([NH:26][C@@H:27]([C:32](O)=[O:33])[C@@H:28]([CH2:30][CH3:31])[CH3:29])=[O:25])[CH:13](CC1C=CC=CC=1)[C:14](=[O:16])[OH:15])=O)C1C=CC=CC=1.Cl.[CH3:36][O:37][CH2:38][C@H:39]([NH2:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>>[CH3:36][O:37][CH2:38][C@H:39]([NH:46][C:32](=[O:33])[C@@H:27]([... | C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C(O)=O)CC1=CC=CC=C1)C(=O)N[C@H]([C@H](C)CC)C(=O)O.Cl.COC[C@@H](C1=CC=CC=C1)N | N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-isoleucine;(R)-α-methoxymethylbenzylamine hydrochloride | 0.0;0.0 | mol;mol | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COC[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](N)CC(O)=O)=O)[C@H](C)CC)=O | α-L-aspartyl-D-isoleucine (R)-α-methoxymethylbenzylamide | null | null | 22.1 |
ord-12a035e31d384b0d952ee7e106393c5e | C(OC([NH:11][C@H:12]([C:24]([NH:26][C@@H:27]([C:29](O)=[O:30])[CH3:28])=[O:25])[CH:13](CC1C=CC=CC=1)[C:14](=[O:16])[OH:15])=O)C1C=CC=CC=1.Cl.[CH3:33][O:34][CH2:35][C@H:36]([NH2:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[CH3:33][O:34][CH2:35][C@H:36]([NH:43][C:29](=[O:30])[C@@H:27]([CH3:28])[NH:26][C:24](=[O:2... | C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C(O)=O)CC1=CC=CC=C1)C(=O)N[C@H](C)C(=O)O.Cl.COC[C@@H](C1=CC=CC=C1)N | N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-alanine;(R)-α-methoxymethylbenzylamine hydrochloride | 0.0;0.0 | mol;mol | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COC[C@@H](C1=CC=CC=C1)NC([C@H](NC([C@@H](N)CC(O)=O)=O)C)=O | α-L-aspartyl-D-alanine-(R)-α-methoxymethylbenzylamide | null | null | 57.3 |
ord-d6db1ba811484e3384ed2f23fdfc613c | [P:1]([O-:5])([O-:4])([O-:3])=[O:2].[Na+].[Na+].[Na+].[Cl-].[Ca+2:10].[Cl-]>O>[P:1]([O-:5])([O-:4])([O-:3])=[O:2].[Ca+2:10].[Ca+2:10].[Ca+2:10].[P:1]([O-:5])([O-:4])([O-:3])=[O:2] |f:0.1.2.3,4.5.6,8.9.10.11.12| | P(=O)([O-])([O-])[O-].[Na+].[Na+].[Na+].[Cl-].[Ca+2].[Cl-] | sodium phosphate;calcium chloride | 0.0;45.3 | mol;g | O.O.O | water;water;water | 300.0;300.0;200.0 | g;g;g | null | null | null | null | null | null | null | null | null | null | P(=O)([O-])([O-])[O-].[Ca+2].[Ca+2].[Ca+2].P(=O)([O-])([O-])[O-] | tricalcium phosphate | null | null | null |
ord-a5d5cdb2b6f74613b95722ef03582f33 | [P:1]([O-:5])([O-:4])([O-:3])=[O:2].[Na+].[Na+].[Na+].[Cl-].[Ca+2:10].[Cl-]>O>[P:1]([O-:5])([O-:4])([O-:3])=[O:2].[Ca+2:10].[Ca+2:10].[Ca+2:10].[P:1]([O-:5])([O-:4])([O-:3])=[O:2] |f:0.1.2.3,4.5.6,8.9.10.11.12| | P(=O)([O-])([O-])[O-].[Na+].[Na+].[Na+].[Cl-].[Ca+2].[Cl-] | sodium phosphate;calcium chloride | 0.0;45.3 | mol;g | O.O.O | water;water;water | 300.0;300.0;200.0 | g;g;g | null | null | null | null | null | null | null | null | null | null | P(=O)([O-])([O-])[O-].[Ca+2].[Ca+2].[Ca+2].P(=O)([O-])([O-])[O-] | tricalcium phosphate | null | null | null |
ord-1486324d16694ddca5c93306441d16d7 | [P:1]([O-:5])([O-:4])([O-:3])=[O:2].[Na+].[Na+].[Na+].[Cl-].[Ca+2:10].[Cl-]>O>[P:1]([O-:5])([O-:4])([O-:3])=[O:2].[Ca+2:10].[Ca+2:10].[Ca+2:10].[P:1]([O-:5])([O-:4])([O-:3])=[O:2] |f:0.1.2.3,4.5.6,8.9.10.11.12| | P(=O)([O-])([O-])[O-].[Na+].[Na+].[Na+].[Cl-].[Ca+2].[Cl-] | sodium phosphate;calcium chloride | 0.0;45.3 | mol;g | O.O.O | water;water;water | 300.0;300.0;200.0 | g;g;g | null | null | null | null | null | null | null | null | null | null | P(=O)([O-])([O-])[O-].[Ca+2].[Ca+2].[Ca+2].P(=O)([O-])([O-])[O-] | tricalcium phosphate | null | null | null |
ord-59691e7705044240a0b61a8537732528 | [P:1]([O-:5])([O-:4])([O-:3])=[O:2].[Na+].[Na+].[Na+].[Cl-].[Ca+2:10].[Cl-]>O>[P:1]([O-:5])([O-:4])([O-:3])=[O:2].[Ca+2:10].[Ca+2:10].[Ca+2:10].[P:1]([O-:5])([O-:4])([O-:3])=[O:2] |f:0.1.2.3,4.5.6,8.9.10.11.12| | P(=O)([O-])([O-])[O-].[Na+].[Na+].[Na+].[Cl-].[Ca+2].[Cl-] | sodium phosphate;calcium chloride | 0.0;22.65 | mol;g | O.O.O.O.O | water;Solution A;water;Solution B;water | 150.0;0.0;150.0;0.0;200.0 | g;mol;g;mol;g | null | null | null | null | null | null | null | null | null | null | P(=O)([O-])([O-])[O-].[Ca+2].[Ca+2].[Ca+2].P(=O)([O-])([O-])[O-] | tricalcium phosphate | null | null | null |
ord-d6f09b988e0848769dd846f380d71108 | [OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH:13]1[O:18][CH2:17][CH2:16][CH2:15][O:14]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.C(#N)C>[O:14]1[CH2:15][CH2:16][CH2:17][O:18][CH:13]1[CH2:12][CH2:11][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1 |f:2.3,4.5.6| | OC1=CC=C(C=O)C=C1.BrCCC1OCCCO1.[I-].[K+].C([O-])([O-])=O.[K+].[K+] | 4-hydroxybenzaldehyde;2-(2-bromoethyl)-1,3-dioxane;potassium iodide;potassium carbonate | 13.8;21.1;1.8;35.8 | g;g;g;g | C(C)(=O)OCC.C(C)#N | ethyl acetate;acetonitrile | 200.0;120.0 | mL;mL | null | null | null | null | null | null | null | null | null | null | O1C(OCCC1)CCOC1=CC=C(C=O)C=C1 | 4-(2-[1,3]-dioxane-2-yl-ethoxy)benzaldehyde | 25.6 | g | 100.2 |
ord-7962a8e3cbfa49e3aabf54e37edc9672 | [CH3:1]C(C)([O-])C.[K+].[O:7]1[CH2:12][CH2:11][CH2:10][O:9][CH:8]1[CH2:13][CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>[CH:20]([C:19]1[CH:22]=[CH:23][C:16]([O:15][CH2:14][CH2:13][CH:8]2[O:9][CH2:10][CH2:11][CH2:12][O:7]2)=[CH:17][CH:18]=1)... | CC(C)([O-])C.[K+].O1C(OCCC1)CCOC1=CC=C(C=O)C=C1 | potassium tert-butoxide;4-(2-[1,3]-dioxane-2-yl-ethoxy)benzaldehyde | 18.0;25.6 | g;g | CCOCC.CCOCC | ether;ether | 500.0;200.0 | mL;mL | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | methyl triphenylphosphonium bromide | 57.2 | g | null | null | null | null | null | null | C(=C)C1=CC=C(OCCC2OCCCO2)C=C1 | 2-[2-(4-vinylphenoxy)ethyl]-[1,3]-dioxane | 19.7 | g | 77.6 |
ord-ab767623531e408bb0c0320b5128145a | [OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH:13]1[O:18][CH2:17][CH2:16]C[O:14]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.C(#N)C>[O:18]1[CH2:17][CH2:16][O:14][CH:13]1[CH2:12][CH2:11][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1 |f:2.3,4.5.6| | OC1=CC=C(C=O)C=C1.BrCCC1OCCCO1.[I-].[K+].C([O-])([O-])=O.[K+].[K+] | 4-hydroxybenzaldehyde;2-(2-bromoethyl)-1,3-dioxane;potassium iodide;potassium carbonate | 13.8;19.9;1.8;35.8 | g;g;g;g | C(C)(=O)OCC.C(C)#N | ethyl acetate;acetonitrile | 200.0;120.0 | mL;mL | null | null | null | null | null | null | null | null | null | null | O1C(OCC1)CCOC1=CC=C(C=O)C=C1 | 4-(2-[1,3]-dioxolan-2-yl-ethoxy)benzaldehyde | 23.7 | g | 104.5 |
ord-09284bc5f4434b24a76abcd1557a624c | [CH3:1]C(C)([O-])C.[K+].[O:7]1[CH2:11][CH2:10][O:9][CH:8]1[CH2:12][CH2:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>[CH:19]([C:18]1[CH:21]=[CH:22][C:15]([O:14][CH2:13][CH2:12][CH:8]2[O:9][CH2:10][CH2:11][O:7]2)=[CH:16][CH:17]=1)=[CH2:1] |f:0.1,... | CC(C)([O-])C.[K+].O1C(OCC1)CCOC1=CC=C(C=O)C=C1 | potassium tert-butoxide;4-(2-[1,3]-dioxolan-2-yl-ethoxy)benzaldehyde | 18.0;23.7 | g;g | CCOCC.CCOCC | ether;ether | 500.0;200.0 | mL;mL | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | methyl triphenylphosphonium bromide | 57.2 | g | null | null | null | null | null | null | C(=C)C1=CC=C(OCCC2OCCO2)C=C1 | 2-[2-(4-vinylphenoxy)ethyl]-[1,3]-dioxolan | 20.8 | g | 88.5 |
ord-ddf67391f0ff4ca08b0e3124c9c5cf53 | [CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8].[OH:9][CH2:10]C1C(O)=C(CO)C=C(C)C=1.O.O.C(O)(=O)C(O)=O.CCOCCOC(C)=O.C=O>O>[C:1]1([CH:10]=[O:9])[C:2]([CH3:8])=[CH:3][CH:4]=[CH:5][C:6]=1[OH:7] |f:2.3.4| | CCOCCOC(=O)C.C1=C(C=CC=C1O)C.OCC1=CC(=CC(=C1O)CO)C.O.O.C(C(=O)O)(=O)O.C=O | ethyl cellosolve acetate;m-cresol;2,6-bis(hydroxymethyl)-p-cresol;oxalic acid dihydrate;formaldehyde | 200.0;519.0;538.2;20.0;32.6 | mL;g;g;g;g | O | water | 0.0 | mol | null | null | null | null | null | null | null | null | 70.0 | null | C=1(C(=CC=CC1O)C)C=O | m-cresol formaldehyde | null | null | null |
ord-3c799edf560b44e4b1b3a6fde9733781 | [C:1]([O:9][CH2:10][CH:11](CC)[CH2:12][CH:13]([OH:16])[CH2:14][CH3:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[CH2:20]1[CH2:24]OC(N2C(=O)NC(=O)C(F)=C2)[CH2:21]1.[CH3:34][CH2:35][C:36]1([OH:49])[N:41]=[C:40]([C:42]2[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=2)[Se:39][CH2:38][CH2:37]1>C(OCC)(=O)C>[C:1]([O... | .CCC1(CC[Se]C(=N1)C2=CC=C(C=C2)C)O.O.CCC1(CC[Se]C(=N1)C2=CC=C(C=C2)C)O.O.C1CC(OC1)N2C=C(C(=O)NC2=O)F.O.C1CC(OC1)N2C=C(C(=O)NC2=O)F.CCC1(CC[Se]C(=N1)C2=CC=C(C=C2)C)O.C(C1=CC=CC=C1)(=O)OCC(CC(CC)O)CC.CCC1(CC[Se]C(=N1)C2=CC=C(C=C2)C)O | zirconia;TS-2;water;TS-2;water;TS-1;water;TS-1;TS-2;4-hydroxy-(2'-ethylhexyl) benzoate;TS-2 | 0.0;12.0;66.0;0.0;74.9;15.0;35.9;0.0;18.0;0.0;0.0 | mol;g;g;mol;g;g;g;mol;g;mol;mol | C(C)(=O)OCC | ethyl acetate | 24.0 | g | null | null | null | null | null | null | null | null | null | 123 | C(C1=CC=CC=C1)(=O)OCCCC(CCCCC)O | 4-hydroxy-nonyl benzoate | null | null | null |
ord-bfcf42b524d14d69860f018538be3094 | OC1[CH:7]=[CH:6][C:5]([C:8]2([C:21]3[CH:26]=CC(O)=CC=3)[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:14]3C2=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:4]C=1.C1(=O)O[CH2:31][CH2:30][O:29]1.[C:34](=[O:37])([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>>[OH:29][CH2:30][CH2:31][O:37][C:34]1[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=1[C:1... | OC1=CC=C(C=C1)C1(C2=CC=CC=C2C=2C=CC=CC12)C1=CC=C(C=C1)O.C1(OCCO1)=O.C([O-])([O-])=O.[K+].[K+].C1COCCOCCOCCOCCOCCO1 | 9,9-bis(4-hydroxyphenyl)fluorene;ethylene carbonate;potassium carbonate;18-crown-6 | 84.4;46.7;3.3;0.0 | g;g;g;mol | null | xylenes | 400.0 | mL | null | null | null | null | null | null | null | null | ambient | 6 | OCCOC1=C(C=CC=C1)C1=CC=CC=2CC3=CC=CC=C3C12 | white powder | 70.4 | g | 970.1 |
ord-a9328cbc649c44739edcb5b4674d8842 | [Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8](Cl)(=[O:14])/[CH:9]=[CH:10]/[C:11](Cl)=O.[CH2:16]=[CH2:17]>OS(O)(=O)=O.[Zn].CC(O)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:11]2[O:14][C:8]([C:16]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:17]=3)=[CH:9][CH:10]=2)=[CH:4][CH:3]=1 |f:4.5| | .C=C..BrC1=CC=CC=C1.C(\C=C\C(=O)Cl)(=O)Cl.. | 1,4-di-p-bromophenyl-1,4-butanedione;ethylene;trans-di-p-bromobenzoylethylene;bromobenzene;fumaryl chloride;1,4-diketone;water ice | 0.0;0.0;0.0;0.0;0.0;7.9;1000.0 | mol;mol;mol;mol;mol;g;mL | null | null | null | null | [Zn].CC(=O)O.OS(=O)(=O)O | Zn HOAc;H2SO4 | 0.0;0.0 | mol;mol | null | null | null | null | null | 0.0833 | BrC1=CC=C(C=C1)C=1OC(=CC1)C1=CC=C(C=C1)Br | 2,5-Bis(p-bromophenyl) furan | null | null | null |
ord-523a53f4b10c44568fb08b813772adeb | Br[CH:2]([C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)[CH:3](Br)[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1.[CH3:23][C:24]1[CH:30]=[CH:29][C:27]([O-:28])=[CH:26][CH:25]=1.[Na+].CC1C=CC(O)=CC=1>C1COCC1>[C:24]1([CH3:23])[CH:30]=[CH:29][C:27]([O:28][C:2]([C:14](=[O:22])[C:15]2[... | BrC(C(C(C1=CC=C(C=C1)Br)=O)Br)C(C1=CC=C(C=C1)Br)=O.CC1=CC=C([O-])C=C1.[Na+]..CC1=CC=C(C=C1)O | 1,2-dibromo-1,2-di(4-bromobenzoyl) ethane;sodium 4-methyl phenoxide;Na;4-methylphenol | 11.1;30.0;0.04;0.04 | g;mL;mol;mol | C1CCOC1.C1CCOC1 | THF;THF | 0.0;35.0 | mol;mL | null | null | null | null | null | null | null | null | null | null | C1(=CC=C(C=C1)OC(=CC(C1=CC=C(C=C1)Br)=O)C(C1=CC=C(C=C1)Br)=O)C | 1-(4-tolyloxyl)-1,2-bis(4-bromobenzoyl)ethylene | null | null | null |
ord-67300f99f22241ef9811a9c1212c4492 | [C:1]1([CH3:28])[CH:6]=[CH:5][C:4]([O:7][C:8]([C:19](=O)[C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)=[CH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=2)=[CH:3][CH:2]=1.[K+].[Br-]>P(Cl)(Cl)Cl>[Br:26][C:23]1[CH:22]=[CH:21][C:20]([C:19]2[O:18][C:10]([C:11]3[CH:12]=[CH:13][C:14]([Br:17])... | C1(=CC=C(C=C1)OC(=CC(C1=CC=C(C=C1)Br)=O)C(C1=CC=C(C=C1)Br)=O)C.[K+].[Br-] | 1-(4-tolyloxy)-1,2-bis-(4-bromobenzoyl)ethylene;KBr | 5.0;0.0 | g;mol | P(Cl)(Cl)Cl | phosphorus trichloride | 10.0 | mL | null | null | null | null | null | null | null | null | null | null | BrC1=CC=C(C=C1)C=1OC(=CC1OC1=CC=C(C=C1)C)C1=CC=C(C=C1)Br | 2,5-bis(4-Bromophenyl)-3-(p-tolyloxy)furan | null | null | null |
ord-68a4112e542d4a8cb9aa4b70a263e0cb | Br[CH:2]([C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)[CH:3](Br)[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1.[CH3:23][O-:24].[Na+].[K+].[Br-]>CO>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([CH:3]([O:24][CH3:23])[CH2:2][C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH... | [K+].[Br-].BrC(C(C(C1=CC=C(C=C1)Br)=O)Br)C(C1=CC=C(C=C1)Br)=O.C[O-].[Na+]. | KBr;1,2-dibromo-1,2-di(4-bromobenzoyl) ethane;sodium methoxide;methanol-ether | 0.0;11.1;0.0;0.0 | mol;g;mol;mol | CO.CO | methanol;methanol | 150.0;50.0 | mL;mL | null | null | null | null | null | null | null | null | null | null | BrC1=CC=C(C(=O)C(CC(C2=CC=C(C=C2)Br)=O)OC)C=C1 | 1,2-Bis(4-bromobenzoyl)-1-methoxyethane | null | null | null |
ord-4d66dfcc15f145d887e1d654294844a8 | N1CCCN=C1C1C=CC([C:13]2[O:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[NH:25][CH2:26][CH2:27][CH2:28][N:29]=4)=[CH:20][CH:19]=3)=[CH:16][CH:17]=2)=CC=1.[CH:30]1C(C2NC3C=C(C(N)=N)C=CC=3C=2)=CC=C(C(N)=N)C=1.CN1CCN(C2C=CC3NC(C4C=[CH:69][C:70]5[NH:75][C:74]([C:76]6[CH:77]=[CH:78][C:79](O)=[CH:80][CH:81]=6)=[N:73][C:71]=5... | N1C(=NCCC1)C1=CC=C(C=C1)C=1OC(=CC1)C1=CC=C(C=C1)C=1NCCCN1.C1=CC(=CC=C1C2=CC=3C=CC(=CC3N2)C(=N)N)C(=N)N.CN1CCN(CC1)C=2C=CC3=C(C2)N=C(N3)C=4C=CC5=C(C4)N=C(N5)C=6C=CC(=CC6)O | 2,5-bis[4-(1,4,5,6-tetrahydropyrimidin-2-yl)phenyl] furan;DAPI;Hoechst 33258 | 0.0;0.0;0.0 | mol;mol;mol | null | null | null | null | null | null | null | null | null | null | null | null | null | null | N1C(=NCCCC1)C1=CC=C(C=C1)C=1OC(=CC1)C1=CC=C(C=C1)C=1NCCCCN1 | 2,5-bis [4-(4,5,6,7-tetrahydro-1H-1,3-diazepin-2-yl) phenyl] furan | null | null | null |
ord-a502aa411b624e959a294d1ade8139de | [ClH:1].[NH2:2][CH:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][NH2:8].S([O-])([O-])(=O)=O.[NH4+].[NH4+].P([O-])(O)(O)=O.[K+].S([O-])([O-])(=O)=O.[Mg+2].Cl>>[ClH:1].[NH2:2][C@@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][NH2:8] |f:0.1,2.3.4,5.6,7.8,10.11| | S(=O)(=O)([O-])[O-].[Mg+2].Cl.NC(CCCCN)C(=O)O.S(=O)(=O)([O-])[O-].[NH4+].[NH4+].Cl.P(=O)(O)(O)[O-].[K+] | magnesium sulfate;DL-lysine monohydrochloride;ammonium sulfate;hydrochloric acid;potassium dihydrogen phosphate | 0.0;0.0;0.0;0.0;0.0 | mol;mol;mol;mol;mol | null | null | null | null | null | null | null | null | null | null | null | null | null | 0.1667 | Cl.N[C@H](CCCCN)C(=O)O | D-lysine monohydrochloride | 5.8 | g | null |
ord-bea45d3f17ff4aeeb2836945fd80d389 | [ClH:1].[NH2:2][CH:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][NH2:8].N[C@H](C(O)=O)CCCCN>>[ClH:1].[NH2:2][C@@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][NH2:8] |f:0.1,3.4| | Cl.NC(CCCCN)C(=O)O.N[C@@H](CCCCN)C(=O)O | DL-lysine monohydrochloride;L-lysine | 0.0;0.0 | mol;mol | null | null | null | null | null | null | null | null | null | null | null | null | null | 0.1667 | Cl.N[C@H](CCCCN)C(=O)O | D-lysine monohydrochloride | 14.2 | g | null |
ord-9053e57f398646fcad52b73dfd0e8b51 | [Br:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[N:5]=[CH:6][C:7]=1Br.[CH3:11][O-:12].[Na+]>CO>[Br:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[N:5]=[CH:6][C:7]=1[O:12][CH3:11] |f:1.2| | BrC=1C(N(N=CC1Br)C)=O.C[O-].[Na+]. | 4,5-Dibromo-2-methyl-3(2H)-pyridazinone;sodium methoxide;solution | 20.0;0.0;0.0 | g;mol;mol | CO.CO | methanol;methanol | 0.0;200.0 | mol;mL | null | null | null | null | null | null | null | null | 23.0 | 3 | BrC=1C(N(N=CC1OC)C)=O | desired product | 17 | g | null |
ord-415b27028875405d86f41fbc30253639 | Br[C:2]1[CH:3]=[C:4]([CH3:15])[C:5]2[S:10][CH2:9][CH2:8][C:7]([CH3:12])([CH3:11])[C:6]=2[C:13]=1[CH3:14].C([Li])CCC.CN(C)[CH:23]=[O:24].Cl>C(OCC)C>[CH3:11][C:7]1([CH3:12])[C:6]2[C:13]([CH3:14])=[C:2]([CH:23]=[O:24])[CH:3]=[C:4]([CH3:15])[C:5]=2[S:10][CH2:9][CH2:8]1 | Cl.C(CCC)[Li].BrC=1C=C(C2=C(C(CCS2)(C)C)C1C)C.CN(C=O)C | Hydrochloric acid;n-butyllithium;6-Bromo-3,4-dihydro-4,4,5,8-tetramethyl-2H-1-benzothiopyran;Dimethylformamide | 100.0;42.0;19.8;16.0 | mL;mL;g;mL | C(C)OCC | diethyl ether | 350.0 | mL | null | null | null | null | null | null | null | null | ambient | 1 | CC1(CCSC2=C1C(=C(C=C2C)C=O)C)C | desired compound | 7.7 | g | null |
ord-bbaa547034cb4578bce2648d1c091a1f | [CH3:1][S-:2].[Na+].[Cl:4][C:5]1[CH:10]=[C:9](Cl)[N:8]=[C:7]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:6]=1>C1COCC1>[Cl:4][C:5]1[CH:10]=[C:9]([S:2][CH3:1])[N:8]=[C:7]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:6]=1 |f:0.1| | C[S-].[Na+].ClC1=NC(=NC(=C1)Cl)OCC1=CC=CC=C1 | sodium thiomethoxide;4,6-dichloro-2-(phenylmethoxy)pyrimidine | 2.75;0.0 | g;mol | C1CCOC1 | THF | 0.0 | mol | null | null | null | null | null | null | null | null | null | null | ClC1=NC(=NC(=C1)SC)OCC1=CC=CC=C1 | 4-chloro-6-methylthio-2-(phenylmethoxy)pyrimidine | null | null | null |
ord-3d58caaef3e54ab9bff64df1e59b26f5 | [F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].Cl[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH3:22])[N:16]=1>C1COCC1>[CH3:22][S:21][C:17]1[N:18]=[C:19]([O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=2)[CH:20]=[CH:15][N:16]=1 |f:1.2| | [H-].[Na+].ClC1=NC(=NC=C1)SC.FC(C=1C=C(C=CC1)O)(F)F | NaH;4-chloro-2-(methylthio)pyrimidine;3-(trifluoromethyl)phenol | 1.12;0.0;4.54 | g;mol;g | C1CCOC1 | THF | 0.0 | mol | null | null | null | null | null | null | null | null | null | null | CSC1=NC=CC(=N1)OC1=CC(=CC=C1)C(F)(F)F | phenoxide | null | null | null |
ord-0c41a886f892437a80e1ebfc69bc8999 | [CH2:1]([OH:3])[CH3:2].[H-].[Na+].Cl[C:7]1[CH:12]=[C:11](Cl)[N:10]=[C:9]([S:14][CH3:15])[N:8]=1.[F:16][C:17]([F:26])([F:25])[C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1>C1COCC1.CN(C=O)C>[CH2:1]([O:3][C:7]1[CH:12]=[C:11]([O:24][C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:16])([F:25])[F:26])[CH:19]=2)[N:10]=[... | C(C)O.[H-].[Na+].FC(C=1C=C(C=CC1)O)(F)F.[H-].[Na+].ClC1=NC(=NC(=C1)Cl)SC | Ethanol;NaH;m-trifluoromethyl-phenol;NaH;4,6-dichloro-2-methylthiopyrimidine | 1.18;1.02;6.23;1.54;0.0 | g;g;g;g;mol | C1CCOC1.CN(C)C=O | THF;DMF | 0.0;0.0 | mol;mol | null | null | null | null | null | null | null | null | ambient | 0.5 | C(C)OC1=NC(=NC(=C1)OC1=CC(=CC=C1)C(F)(F)F)SC | 4-ethoxy-2-methylthio-6-[3-(trifluoromethyl)phenoxy]pyrimidine | null | null | null |
ord-779700042b074f55b42f3a2202e7c555 | [F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].Cl[C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[N:18]=[C:17]([S:25][CH3:26])[N:16]=1>C1COCC1>[CH3:26][S:25][C:17]1[N:18]=[C:19]([C:21]([F:24])([F:22])[F:23])[CH:20]=[C:15]([O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11]... | FC(C=1C=C(C=CC1)O)(F)F.[H-].[Na+].ClC1=NC(=NC(=C1)C(F)(F)F)SC | m-(Trifluoromethyl)phenol;NaH;4-chloro-2-methylthio-6-(trifluoromethyl)pyrimidine | 1.06;0.26;0.0 | g;g;mol | C1CCOC1 | THF | 0.0 | mol | null | null | null | null | null | null | null | null | null | null | CSC1=NC(=CC(=N1)C(F)(F)F)OC1=CC(=CC=C1)C(F)(F)F | 2-methylthio-4-trifluoromethyl-6-[3-(trifluoromethyl)phenoxy]pyrimidine | null | null | null |
ord-3df2c010cc0541928156900e8959ed27 | [F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[Br:14][C:15]1[CH:20]=[C:19](Br)[N:18]=[C:17]([S:22][CH3:23])[N:16]=1>C1COCC1>[Br:14][C:15]1[CH:20]=[C:19]([O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=2)[N:18]=[C:17]([S:22][CH3:23])[N:16]=1 |f:1.2| | FC(C=1C=C(C=CC1)O)(F)F.[H-].[Na+].BrC1=NC(=NC(=C1)Br)SC | m-(trifluoromethyl)phenol;NaH;4,6-dibromo-2-(methylthio)pyrimidine | 1.3;0.32;0.0 | g;g;mol | C1CCOC1 | THF | 0.0 | mol | null | null | null | null | null | null | null | null | null | null | BrC1=NC(=NC(=C1)OC1=CC(=CC=C1)C(F)(F)F)SC | phenoxide | null | null | null |
ord-1754134a9e1b4ab5a610540df5e81abc | [CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH2:11])[C:7]=1[C:8]([OH:10])=[O:9].[OH-].[Na+].[C:14](OC(=O)C)(=[O:16])[CH3:15].Cl>O>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH:11][C:14](=[O:16])[CH3:15])[C:7]=1[C:8]([OH:10])=[O:9] |f:1.2| | Cl.CC=1C=CC=C(C1C(=O)O)N.[OH-].[Na+].C(C)(=O)OC(C)=O | HCl;6-methylanthranilic acid;NaOH;acetic anhydride | 0.0;90.6;24.8;63.4 | mol;g;g;g | O | water | 500.0 | mL | null | null | null | null | null | null | null | null | null | 1 | CC1=C(C(=O)O)C(=CC=C1)NC(C)=O | 2-Methyl-6-acetamidobenzoic acid | null | null | null |
ord-036dc1bd98f447088e22557193b51876 | [N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[C:7]=1[C:8]([OH:10])=[O:9]>O>[CH3:5][C:6]1[C:14]([N+:1]([O-:4])=[O:2])=[CH:13][CH:12]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[C:7]=1[C:8]([OH:10])=[O:9] | [N+](=O)(O)[O-].CC1=C(C(=O)O)C(=CC=C1)NC(C)=O. | nitric acid;2-methyl-6-acetamidobenzoic acid;ice | 271.0;106.0;540.0 | mL;g;g | O | water | 270.0 | mL | null | null | null | null | null | null | null | null | 10.0 | 1 | CC1=C(C(=O)O)C(=CC=C1[N+](=O)[O-])NC(C)=O | 2-Methyl-3-nitro-6-acetamidobenzoic acid | null | null | null |
ord-36a2a540166a44e2ae3ef4e91516ef3a | [CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([NH:14]C(=O)C)[C:3]=1[C:4]([OH:6])=[O:5].Cl>[OH-].[Na+]>[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([NH2:14])[C:3]=1[C:4]([OH:6])=[O:5] |f:2.3| | CC1=C(C(=O)O)C(=CC=C1[N+](=O)[O-])NC(C)=O.Cl | 2-methyl-3-nitro-6-acetamidobenzoic acid;HCl | 75.6;425.0 | g;mL | [OH-].[Na+] | NaOH | 450.0 | mL | null | null | null | null | null | null | null | null | 95.0 | 1 | CC1=C(C(=O)O)C(=CC=C1[N+](=O)[O-])N | 2-Methyl-3-nitro-6-aminobenzoic acid | null | null | null |
ord-24a3ddd0c4da4019a874af8b0e5c2e2d | [CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([NH2:14])[C:3]=1[C:4]([OH:6])=[O:5].[C:15](=O)([O-])O.[Na+].C(=O)=O.S(OC)(OC)(=O)=O.[Na]>CC(C)=O.O>[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([NH2:14])[C:3]=1[C:4]([O:6][CH3:15])=[O:5] |f:1.2,^1:29| | C(=O)=O.S(=O)(=O)(OC)OC.[Na].CC1=C(C(=O)O)C(=CC=C1[N+](=O)[O-])N.C(O)([O-])=O.[Na+].CC1=C(C(=O)O)C(=CC=C1[N+](=O)[O-])N | CO2;dimethyl sulfate;sodium;2-methyl-3-nitro-6-aminobenzoic acid;sodium hydrogen carbonate;2-methyl-3-nitro-6-aminobenzoic acid | 0.0;35.3;0.0;0.0;43.0;49.7 | mol;g;mol;mol;g;g | CC(=O)C.O.CC(=O)C | acetone;water;acetone | 0.0;1800.0;380.0 | mol;mL;mL | null | null | null | null | null | null | null | null | null | null | CC1=C(C(=O)OC)C(=CC=C1[N+](=O)[O-])N | Methyl 2-methyl-3-nitro-6-aminobenzoate | null | null | null |
ord-9750ebabdd9f4e72aa5a98408ce4247f | [NH3:1].O.C[O:4][C:5]([C:7]1[C:12]([CH3:13])=[C:11]([N+:14]([O-:16])=[O:15])[CH:10]=[CH:9][C:8]=1[S:17](Cl)(=[O:19])=[O:18])=O>O1CCCC1>[CH3:13][C:12]1[C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=[C:8]2[C:7]=1[C:5](=[O:4])[NH:1][S:17]2(=[O:19])=[O:18] | N.O.COC(=O)C1=C(C=CC(=C1C)[N+](=O)[O-])S(=O)(=O)Cl | ammonia;water;2-methoxycarbonyl-3-methyl-4-nitrobenzenesulfonyl chloride | 104.0;100.0;48.7 | mL;mL;g | O1CCCC1 | tetrahydrofuran | 70.0 | mL | null | null | null | null | null | null | null | null | 25.0 | 3 | CC1=C2C(NS(=O)(=O)C2=CC=C1[N+](=O)[O-])=O | 4-Methyl-5-nitrosaccharin | null | null | null |
ord-67ec3bcdf85a4cd095b46cc07afa68ed | [CH3:1][C:2]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[C:9]2[C:3]=1[C:4](=[O:16])[NH:5][S:6]2(=[O:8])=[O:7].[H][H]>O.[Pd]>[CH3:1][C:2]1[C:12]([NH2:13])=[CH:11][CH:10]=[C:9]2[C:3]=1[C:4](=[O:16])[NH:5][S:6]2(=[O:8])=[O:7] | CC1=C2C(NS(=O)(=O)C2=CC=C1[N+](=O)[O-])=O.[H][H] | 4-methyl-5-nitrosaccharin;Hydrogen | 33.6;0.0 | g;mol | O | water | 1200.0 | mL | [Pd] | Pd/C | 5.0 | g | null | null | null | null | 45.0 | null | CC1=C2C(NS(=O)(=O)C2=CC=C1N)=O | 4-Methyl-5-aminosaccharin | null | null | null |
ord-64895c5b03224120a7cbd0bc650559fc | Cl.[CH3:2][C:3]1[C:13](N)=[CH:12][CH:11]=[C:10]2[C:4]=1[C:5](=[O:15])[NH:6][S:7]2(=[O:9])=[O:8].N([O-])=O.[Na+].[I-:20].[K+]>O.C(O)(=O)C>[CH3:2][C:3]1[C:13]([I:20])=[CH:12][CH:11]=[C:10]2[C:4]=1[C:5](=[O:15])[NH:6][S:7]2(=[O:9])=[O:8] |f:2.3,4.5| | .Cl.[I-].[K+].CC1=C2C(NS(=O)(=O)C2=CC=C1N)=O.N(=O)[O-].[Na+] | diazonium salt;HCl;potassium iodide;4-methyl-5-aminosaccharin;sodium nitrite | 0.0;40.0;19.1;23.4;7.9 | mol;mL;g;g;g | O.C(C)(=O)O.O | water;acetic acid;water | 160.0;205.0;170.0 | mL;mL;mL | null | null | null | null | null | null | null | null | 50.0 | null | CC1=C2C(NS(=O)(=O)C2=CC=C1I)=O | iodine | null | null | null |
ord-5bfe10bbdded406ba8ad3cc28a98a377 | [OH-].[Na+].[C:3]([CH:11]([CH2:17][C:18]#[CH:19])[C:12](OCC)=[O:13])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:20][NH:21]O.Cl>O.CO.CCOCC>[CH3:20][N:21]1[C:12](=[O:13])[CH:11]([CH2:17][C:18]#[CH:19])[CH:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[O:10]1 |f:0.1| | [OH-].[Na+].CNO.C(C1=CC=CC=C1)(=O)C(C(=O)OCC)CC#C.[OH-].[Na+].Cl | NaOH;N-methylhydroxylamine;ethyl α-benzoyl-α-propargylacetate;NaOH;HCl | 0.54;1.02;1.42;0.28;0.0 | g;g;g;g;mol | O.CO.CCOCC.O.CO | water;methanol;ether;water;methanol | 1.5;2.0;150.0;3.0;7.0 | mL;mL;mL;mL;mL | null | null | null | null | null | null | null | null | -30.0 | 0.1667 | CN1OC(C(C1=O)CC#C)C1=CC=CC=C1 | 2-methyl-5-phenyl-4-propargylisoxazolin-3-one | 0.46 | g | 34.5 |
ord-c014829738084401b0a152f2e7cdf4bb | [CH3:1][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][NH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].CI.[CH3:16]C(C)([O-])C.[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:4][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:16])[CH:10]=1)(=[O:8])=[O:7])([CH3:1])[CH3:3] |f:2.3| | CC(C)(C)NS(=O)(=O)C1=CNC=C1.CI.CC(C)([O-])C.[K+] | N-(1,1-dimethylethyl)-1H-pyrrole-3 -sulfonamide;methyl iodide;potassium t-butoxide | 9.0;3.2;5.43 | g;mL;g | CN(C=O)C.C(C)(=O)OCC | N,N-dimethylforamide;ethyl acetate | 90.0;0.0 | mL;mol | null | null | null | null | null | null | null | null | 60.0 | 2 | CC(C)(C)NS(=O)(=O)C1=CN(C=C1)C | N-(1,1-Dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide | null | null | null |
ord-a32d55e896f94ee09bb5a13e0797fb99 | [CH3:1][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].C([Li])CCC.Cl[C:21]([O:23][CH3:24])=[O:22].Cl>C1COCC1.[Au]>[CH3:4][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10]=1[C:21]([O:23][CH3:24])=[O:22])(=[O:8])=[O:7])([CH3:1])[CH3:3] | CC(C)(C)NS(=O)(=O)C1=CN(C=C1)C.ClC(=O)OC.Cl.C(CCC)[Li] | N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide;Methyl chloroformate;HCl;n-butyllithium | 4.62;0.37;0.0;4.1 | mol;mL;mol;mL | C1CCOC1. | THF;hexanes | 150.0;0.0 | mL;mol | [Au].[Au] | gold;gold | 0.0;0.0 | mol;mol | null | null | null | null | -78.0 | 0.5 | CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)C(=O)OC | title compound | null | null | null |
ord-476d1b77fb1f4defbab1a8181428d9b8 | [CH3:1][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].C([Li])CCC.Cl[C:21]([O:23][CH3:24])=[O:22].Cl>C1COCC1.[Au]>[CH3:4][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10]=1[C:21]([O:23][CH3:24])=[O:22])(=[O:8])=[O:7])([CH3:1])[CH3:3] | Cl.CC(C)(C)NS(=O)(=O)C1=CN(C=C1)C.C(CCC)[Li].ClC(=O)OC | HCl;N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide;n-butyllithium;methyl chloroformate | 0.0;5.0;20.0;1.87 | mol;g;mL;mL | C1CCOC1. | THF;hexanes | 150.0;0.0 | mL;mol | [Au].[Au] | gold;gold | 0.0;0.0 | mol;mol | null | null | null | null | -78.0 | 0.5 | CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)C(=O)OC | title compound | 3.53 | g | 55.9 |
ord-740719404b1e4815a4a77e34574adcd7 | CC([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10]=1[C:15]([O:17][CH3:18])=[O:16])(=[O:8])=[O:7])(C)C.FC(F)(F)C(O)=O>[Au].C(Cl)Cl>[NH2:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10]=1[C:15]([O:17][CH3:18])=[O:16])(=[O:8])=[O:7] | CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)C(=O)OC.FC(C(=O)O)(F)F | methyl 3-[[(1,1-dimethylethyl)amino]-sulfonyl]-1-methyl-1H-pyrrole-2-carboxylate;trifluoroacetic acid | 3.53;80.0 | g;mL | C(Cl)Cl | methylene chloride | 0.0 | mol | [Au] | gold | 0.0 | mol | null | null | null | null | null | null | NS(=O)(=O)C1=C(N(C=C1)C)C(=O)OC | title compound | null | null | null |
ord-ec291f168e3d4ab6bc17d0209ef33361 | [CH3:1][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].C([Li])CCC.[CH3:20][S:21]SC.Cl>C1COCC1>[CH3:4][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10]=1[S:21][CH3:20])(=[O:8])=[O:7])([CH3:1])[CH3:3] | Cl.C(CCC)[Li].CC(C)(C)NS(=O)(=O)C1=CN(C=C1)C.CSSC | HCl;n-butyllithium;N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide;dimethyldisulfide | 0.0;25.52;6.48;2.97 | mol;mL;g;mL | .C1CCOC1 | hexanes;THF | 0.0;150.0 | mol;mL | null | null | null | null | null | null | null | null | -78.0 | 0.5 | CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)SC | title compound | 4.63 | g | 58.8 |
ord-ee7d05a9975a483f9332d56b8ce092a7 | CC([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10]=1[S:15][CH3:16])(=[O:8])=[O:7])(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:14][N:11]1[CH:12]=[CH:13][C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[C:10]1[S:15][CH3:16] | CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)SC.FC(C(=O)O)(F)F | N-(1,1-dimethylethyl)-1-methyl-2-(methylthio)-1H-pyrrole-3-sulfonamide;trifluoroacetic acid | 4.63;50.0 | g;mL | C(Cl)Cl | methylene chloride | 50.0 | mL | null | null | null | null | null | null | null | null | ambient | 16 | CN1C(=C(C=C1)S(=O)(=O)N)SC | title compound | 2.9 | g | 79.6 |
ord-0d425205828e434aa8465064fdc60f2d | [CH3:1][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].C([Li])CCC.[Br:20]Br.Cl>C(OCC)C>[Br:20][C:10]1[N:11]([CH3:14])[CH:12]=[CH:13][C:9]=1[S:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])(=[O:8])=[O:7] | Cl.CC(C)(C)NS(=O)(=O)C1=CN(C=C1)C.C(CCC)[Li].BrBr | HCl;N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide;n-butyllithium;bromine | 0.0;8.85;36.0;2.2 | mol;g;mL;mL | C(C)OCC. | diethyl ether;hexanes | 200.0;0.0 | mL;mol | null | null | null | null | null | null | null | null | -78.0 | 0.25 | BrC=1N(C=CC1S(=O)(=O)NC(C)(C)C)C | title compound | 7.11 | g | 58.7 |
ord-952e75b6acac43568991fc07fe11133a | [Br:1][C:2]1[N:3]([CH3:15])[CH:4]=[CH:5][C:6]=1[S:7]([NH:10]C(C)(C)C)(=[O:9])=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[N:3]([CH3:15])[CH:4]=[CH:5][C:6]=1[S:7]([NH2:10])(=[O:8])=[O:9] | BrC=1N(C=CC1S(=O)(=O)NC(C)(C)C)C.C(=O)(C(F)(F)F)O | 2-bromo-N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide;TFA | 7.11;50.0 | g;mL | C(Cl)Cl | methylene chloride | 50.0 | mL | null | null | null | null | null | null | null | null | ambient | 16 | BrC=1N(C=CC1S(=O)(=O)N)C | title compound | 1.23 | g | 21.4 |
ord-1689ec83ac2b4e2e9bc10359a96a617b | [CH3:1][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].CN(C)[CH:17]=[O:18].Cl>C1COCC1>[CH3:4][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10]=1[CH:17]=[O:18])(=[O:8])=[O:7])([CH3:1])[CH3:3] | CC(C)(C)NS(=O)(=O)C1=CN(C=C1)C.CN(C=O)C.Cl | N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide;N,N-dimethylformamide;HCl | 12.96;4.64;0.0 | g;mL;mol | C1CCOC1. | THF;hexanes | 300.0;0.0 | mL;mol | null | null | null | null | null | null | null | null | -78.0 | 0.5 | CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)C=O | title compound | 5.72 | g | 39 |
ord-3b75f1f1033143b794c5a9db7bc6a994 | Cl.[CH3:2][O:3][NH2:4].C([O-])(=O)C.[Na+].[CH3:10][C:11]([NH:14][S:15]([C:18]1[CH:22]=[CH:21][N:20](C)[C:19]=1[CH:24]=O)(=[O:17])=[O:16])([CH3:13])[CH3:12].O>CO>[CH3:13][C:11]([NH:14][S:15]([C:18]1[CH:22]=[CH:21][NH:20][C:19]=1[CH:24]=[N:4][O:3][CH3:2])(=[O:17])=[O:16])([CH3:10])[CH3:12] |f:0.1,2.3| | O.C(C)(=O)[O-].[Na+].Cl.CON.CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)C=O | water;sodium acetate;methoxyamine hydrochloride;N-(1,1-dimethylethyl)-2-formyl-1-methyl-1H-pyrrole-3-sulfonamide | 500.0;3.84;3.91;5.72 | mL;g;g;g | CO | methanol | 60.0 | mL | null | null | null | null | null | null | null | null | ambient | null | CC(C)(C)NS(=O)(=O)C1=C(NC=C1)C=NOC | title compound | 5.74 | g | 96.2 |
ord-0d13730de7524a88a677102766469c81 | CC([NH:5][S:6]([C:9]1[CH:13]=[CH:12][NH:11][C:10]=1[CH:14]=[N:15][O:16][CH3:17])(=[O:8])=[O:7])(C)C.[C:18](O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:17][O:16][N:15]=[CH:14][C:10]1[N:11]([CH3:18])[CH:12]=[CH:13][C:9]=1[S:6]([NH2:5])(=[O:7])=[O:8] | CC(C)(C)NS(=O)(=O)C1=C(NC=C1)C=NOC.C(=O)(C(F)(F)F)O | N-(1,1-dimethylethyl)-2-[(methoxyimino)-methyl]-1H-pyrrole-3-sulfonamide;TFA | 5.74;75.0 | g;mL | C(Cl)Cl | methylene chloride | 75.0 | mL | null | null | null | null | null | null | null | null | ambient | 16 | CON=CC=1N(C=CC1S(=O)(=O)N)C | title compound | 3.49 | g | null |
ord-00887c12283747658f3f8ff3622cc7d7 | CC([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[CH:10]=1)(=[O:8])=[O:7])(C)C.C([Li])[CH2:16][CH2:17][CH3:18].[S:20](=[O:22])=[O:21].Cl[N:24]1[C:28](=O)CC[C:25]1=O.O1CCC[CH2:32]1>>[CH3:32][C:17]([C:13]1[C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[C:10]([S:20]([N:24]([CH3:28])[CH3:25])(=[O:22])=[O:21])[N:11]([CH3:14])[CH:12... | ClN1C(CCC1=O)=O.C(CCC)[Li].CC(C)(C)NS(=O)(=O)C1=CN(C=C1)C.O1CCCC1..S(=O)=O | N-chlorosuccinimide;n-butyllithium;N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide;tetrahydrofuran;dimethylimine;sulfur dioxide | 0.031;0.0615;6.48;150.0;0.075;0.0 | mol;mol;g;mL;mol;mol | null | hexanes | 0.0 | mol | null | null | null | null | null | null | null | null | ambient | 1 | CC(C)(C)C=1C(=C(N(C1)C)S(=O)(=O)N(C)C)S(=O)(=O)N | title compound | 6.95 | g | null |
ord-bce13e6e0f2b4556bf712059577ecdcd | CC([C:5]1[C:6]([S:17]([NH2:20])(=[O:19])=[O:18])=[C:7]([S:11]([N:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])[N:8]([CH3:10])[CH:9]=1)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:15][N:14]([CH3:16])[S:11]([C:7]1[N:8]([CH3:10])[CH:9]=[CH:5][C:6]=1[S:17]([NH2:20])(=[O:19])=[O:18])(=[O:12])=[O:13] | CC(C)(C)C=1C(=C(N(C1)C)S(=O)(=O)N(C)C)S(=O)(=O)N.C(=O)(C(F)(F)F)O | (1,1-dimethylethyl)-N2,N2,1-trimethyl-1H-pyrrole-2,3-disulfonamide;TFA | 0.0;75.0 | mol;mL | C(Cl)Cl | methylene chloride | 75.0 | mL | null | null | null | null | null | null | null | null | ambient | 16 | CN(S(=O)(=O)C=1N(C=CC1S(=O)(=O)N)C)C | title compound | 4.52 | g | null |
ord-acf44331951a4df6acd00502ec327265 | [CH3:1][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].C([Li])CCC.[CH3:20][N:21]([CH3:25])[C:22](Cl)=[O:23].[Cl-].[NH4+].Cl>C1COCC1>[CH3:4][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10]=1[C:22]([N:21]([CH3:25])[CH3:20])=[O:23])(=[O:8])=[O:7])([CH3:1])[CH3:... | [Cl-].[NH4+].C(CCC)[Li].CC(C)(C)NS(=O)(=O)C1=CN(C=C1)C.CN(C(=O)Cl)C.Cl | ammonium chloride;n-butyllithium;N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide;N,N-dimethylcarbamyl chloride;HCl | 60.0;25.0;6.48;3.1;30.0 | mL;mL;g;mL;mL | .C1CCOC1.C1CCOC1 | hexanes;THF;THF | 0.0;150.0;10.0 | mol;mL;mL | null | null | null | null | null | null | null | null | -78.0 | 0.5 | CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)C(=O)N(C)C | title compound | 4.33 | g | 50.2 |
ord-4d0fbf7c4db24ef2820d2d87a9754e6c | CC([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10]=1[C:15]([N:17]([CH3:19])[CH3:18])=[O:16])(=[O:8])=[O:7])(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10]=1[C:15]([N:17]([CH3:19])[CH3:18])=[O:16])(=[O:8])=[O:7] | CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)C(=O)N(C)C.C(=O)(C(F)(F)F)O | 3-[[(1,1-dimethylethyl)amino]sulfonyl]-N,N,1-trimethyl-1H-pyrrole-2-carboxamide;TFA | 5.63;75.0 | g;mL | C(Cl)Cl | methylene chloride | 75.0 | mL | null | null | null | null | null | null | null | null | ambient | 16 | NS(=O)(=O)C1=C(N(C=C1)C)C(=O)N(C)C | title compound | 4.21 | g | 92.9 |
ord-66c80b7eb0654eda89cb0773db258c7f | [CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[CH:3]1.C([Li])CCC.[S:12](=[O:14])=[O:13].[C:15]([NH2:19])([CH3:18])([CH3:17])[CH3:16]>C1COCC1>[CH3:16][C:15]([NH:19][S:12]([C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=1)(=[O:14])=[O:13])([CH3:18])[CH3:17] | S(=O)=O.C(CCC)[Li]..CN1C=CC=C1.C(C)(C)(C)N | sulfur dioxide;n-butyllithium;hexanes;N-methyl-pyrrole;t-butylamine | 9.0;56.0;0.13;10.0;82.0 | mL;mL;mol;g;mL | C1CCOC1 | THF | 120.0 | mL | null | null | null | null | null | null | null | null | ambient | 16 | CC(C)(C)NS(=O)(=O)C=1N(C=CC1)C | title compound | 7.4 | g | 28.5 |
ord-eaa9d1d720194b459594019c4118fe86 | [CH3:1][C:2]([NH:5][S:6]([C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][CH:13]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].C([Li])CCC.Cl[C:21]([O:23][CH3:24])=[O:22]>C1COCC1.C(OCC)(=O)C>[CH3:4][C:2]([NH:5][S:6]([C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][C:13]=1[C:21]([O:23][CH3:24])=[O:22])(=[O:8])=[O:7])([CH3:1])[CH3:3] | ClC(=O)OC.CC(C)(C)NS(=O)(=O)C=1N(C=CC1)C.C(CCC)[Li] | methyl chloroformate;N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-2-sulfonamide;n-butyllithium | 1.63;2.5;13.0 | g;g;mL | C1CCOC1.C(C)(=O)OCC.C1CCOC1 | THF;ethyl acetate;THF | 6.0;200.0;50.0 | mL;mL;mL | null | null | null | null | null | null | null | null | null | 0.5 | CC(C)(C)NS(=O)(=O)C=1N(C=CC1C(=O)OC)C | title compound | 0.45 | g | 14.3 |
ord-a5a19d2e3ccc4cb7bff13f06f043ffc0 | [NH2:1][S:2]([C:5]1[N:6]([CH3:14])[CH:7]=[CH:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11])(=[O:4])=[O:3].C[O:16][C:17]1N=C(C)[N:20]=[C:19]([NH:24][C:25](=O)[O:26][C:27]2C=CC=CC=2)[N:18]=1.C1CCN2[C:37](=[N:38][CH2:39]CC2)CC1.Cl>C(#N)C.O>[CH3:27][O:26][C:25]1[N:24]=[C:19]([NH:18][C:17]([NH:1][S:2]([C:5]2[N:6]([CH3:14])[CH:7]=[... | Cl.NS(=O)(=O)C=1N(C=CC1C(=O)OC)C.COC1=NC(=NC(=N1)C)NC(OC1=CC=CC=C1)=O.C1CCC2=NCCCN2CC1 | HCl;Methyl 2-(aminosulfonyl)-1-methyl-1H-pyrrole-3-carboxylate;phenyl (4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamate;DBU | 0.5;0.1;0.13;0.075 | mL;g;g;mL | O.C(C)#N | water;acetonitrile | 15.0;2.0 | mL;mL | null | null | null | null | null | null | null | null | ambient | 0.5 | COC=1N=C(NN(C1)C)NC(=O)NS(=O)(=O)C=1N(C=CC1C(=O)OC)C | oil | 0.13 | g | null |
ord-819df65591774363bb9b76f5effae47b | [NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][C:11]([C:13]1[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=1[F:20])=O.[OH-].[K+]>CO>[F:19][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([F:20])[C:13]=1[C:11]1[CH:10]=[CH:4][C:3]2[C:2](=[N:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1 |f:2.3| | NC1=C(C=O)C=CC=N1.CC(=O)C1=C(C=CC=C1F)F.[OH-].[K+] | 2-Aminonicotinaldehyde;2,6-difluoroacetophenone;KOH | 2.44;3.28;3.0 | g;g;mL | CO | MeOH | 20.0 | mL | null | null | null | null | null | null | null | null | null | null | FC1=C(C(=CC=C1)F)C1=NC2=NC=CC=C2C=C1 | desired product | 3.8 | g | 78.4 |
ord-6da8fccbc46d48d9b47085df7224e0c2 | [NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:10]([C:13]1[S:14][CH:15]=[CH:16][N:17]=1)(=O)[CH3:11].[OH-].[K+]>CO>[S:14]1[CH:15]=[CH:16][N:17]=[C:13]1[C:10]1[CH:11]=[CH:4][C:3]2[C:2](=[N:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1 |f:2.3| | NC1=C(C=O)C=CC=N1.C(C)(=O)C=1SC=CN1.[OH-].[K+] | 2-Aminonicotinaldehyde;2-acetylthiazole;KOH | 1.5;1.64;1.5 | g;g;mL | CO | MeOH | 12.0 | mL | null | null | null | null | null | null | null | null | null | 3 | S1C(=NC=C1)C1=NC2=NC=CC=C2C=C1 | desired product | 1.22 | g | 46.5 |
ord-4fe7e7b0295444c08046dd75241f89c9 | [OH:1][N:2]=[C:3]1[CH2:20][C@@:19]2([CH3:21])[C@@H:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[OH:22])[CH2:5][C:4]1=O.[NH2:24][OH:25].Cl.[CH3:27][C:28]([O-:30])=O.[Na+].O>O>[C:28]([O:22][C@H:13]1[CH2:12][CH2:11][C@H:10]2[C@H:9]3[C@H:18]([CH2:17][CH2:16][C@:... | ON=C1C(C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@]2(C1)C)O)=O.NO.Cl.CC(=O)[O-].[Na+].O | steroid;NH2OH.HCl;NaOAc H2O | 0.0;0.0;0.0 | mol;mol;mol | O | H2O | 0.0 | mol | null | null | null | null | null | null | null | null | ambient | null | C(C)(=O)O[C@@H]1[C@]2(C)[C@@H](CC1)[C@@H]1CC[C@H]3CC(C(C[C@]3(C)[C@H]1CC2)=NO)=NO | 17β-Acetoxy-2,3-dihydroxyimino-5α-androstane | null | null | null |
ord-9c0049ffd5bd4c2597bd8dc1da4f9125 | [N+]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]=1[C:6]#[N:7])([O-])=O.[C:15]1([SH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].N1C=CC=CC=1>CN(C=O)C.O>[N+:12]([C:8]1[CH:9]=[CH:10][CH:11]=[C:4]([S:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]=1[C:6]#[N:7])([O-:14])=... | .[N+](=O)([O-])C1=C(C#N)C(=CC=C1)[N+](=O)[O-].C1(=CC=CC=C1)S.C(=O)([O-])[O-].[K+].[K+].N1=CC=CC=C1 | ice water;2,6-dinitrobenzonitrile;thiophenol;K2CO3;Pyridine | 0.0;2.0;1.06;1.44;0.0 | mol;g;mL;g;mol | O.CN(C)C=O | H2O;DMF | 100.0;50.0 | mL;mL | null | null | null | null | null | null | null | null | null | 0.5 | [N+](=O)([O-])C1=C(C#N)C(=CC=C1)SC1=CC=CC=C1 | 2-nitro-6-(phenylthio)benzonitrile | 1.94 | g | 75.7 |
ord-d850da0197e245649bff3ba3999f661f | O.[N+:2]([C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:6]=1[C:7]#[N:8])([O-])=O.Cl[Sn]Cl>COCCOCCOC.Cl>[NH2:2][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:6]=1[C:7]#[N:8] | O.[N+](=O)([O-])C1=C(C#N)C(=CC=C1)SC1=CC=CC=C1.Cl[Sn]Cl | water;2-nitro-6-(phenylthio)benzonitrile;SnCl2 | 0.0;3.9;11.53 | mol;g;g | COCCOCCOC.Cl | diglyme;HCl | 85.0;35.0 | mL;mL | null | null | null | null | null | null | null | null | null | null | NC1=C(C#N)C(=CC=C1)SC1=CC=CC=C1 | 2-Amino-6-(phenylthio)benzonitrile | null | null | null |
ord-942c876021324f25bb9887685a674993 | [N+]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]=1[C:6]#[N:7])([O-])=O.C([O-])([O-])=O.[K+].[K+].[CH3:21][C:22]1[CH:23]=[C:24]([SH:29])[CH:25]=[C:26]([CH3:28])[CH:27]=1.O>CN(C=O)C>[CH3:21][C:22]1[CH:23]=[C:24]([S:29][C:4]2[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:5]=2[C:6]#[N:7])[CH:25]... | O.[N+](=O)([O-])C1=C(C#N)C(=CC=C1)[N+](=O)[O-].C(=O)([O-])[O-].[K+].[K+].CC=1C=C(C=C(C1)C)S | water;2,6-dinitrobenzonitrile;K2CO3;3,5-dimethylthiophenol | 150.0;1.4;1.1;1.1 | mL;g;g;g | CN(C)C=O.CN(C)C=O | DMF;DMF | 10.0;10.0 | mL;mL | null | null | null | null | null | null | null | null | 0.0 | null | CC=1C=C(C=C(C1)C)SC1=C(C#N)C(=CC=C1)[N+](=O)[O-] | 2-[(3,5-dimethylphenyl)thio]-6-nitrobenzonitrile | 1.64 | g | 73,011.2 |
ord-8c04216a28bb4609b9208e0d1a14c091 | [CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[C:11]=2[C:12]#[N:13])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[OH-].[Na+]>COCCOCCOC.Cl.O>[NH2:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:10]([S:9][C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=2)[C:11]=1[C:12]#[N:13] |f:1.2| | CC=1C=C(C=C(C1)C)SC1=C(C#N)C(=CC=C1)[N+](=O)[O-].[OH-].[Na+]. | 2-[(3,5-Dimethylphenyl)thio]-6-nitrobenzonitrile;NaOH;stannous chloride-2H2O | 1.0;12.0;3.16 | g;g;g | COCCOCCOC.O.Cl | diglyme;water;HCl | 50.0;100.0;15.0 | mL;mL;mL | null | null | null | null | null | null | null | null | null | null | NC1=C(C#N)C(=CC=C1)SC1=CC(=CC(=C1)C)C | 2-amino-6-[(3,5-dimethylphenyl)thio]benzonitrile | 0.57 | g | 64 |
ord-a610715a9a2049339b2b5008fb407eed | [F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[C:3]=1[C:4]#[N:5].ClC1C=CC=C(C(OO)=[O:27])C=1.S(=O)(O)[O-].[Na+].[OH2:35]>>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)(=[O:27])=[O:35])[C:3]=1[C:4]#[N:... | ClC1=CC(=CC=C1)C(=O)OO.S([O-])(O)=O.[Na+]..O.FC1=C(C#N)C(=CC=C1)SC1=CC(=CC=C1)OC.ClC1=CC(=CC=C1)C(=O)OO. | m-chloroperbenzoic acid;sodium bisulfite;resultant mixture;water;2-fluoro-6-[(3-methoxyphenyl)thio]benzonitrile;m-chloroperbenzoic acid;resultant mixture | 0.29;0.0;0.0;0.0;2.0;2.93;0.0 | g;mol;mol;mol;g;g;mol | null | null | null | null | null | null | null | null | null | null | null | null | null | null | FC1=C(C#N)C(=CC=C1)S(=O)(=O)C1=CC(=CC=C1)OC | 2-Fluoro-6-[(3 -methoxyphenyl)sulfonyl]benzonitrile | null | null | null |
ord-70d2fe8819214856a573963ea6b87bb1 | F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)(=[O:12])=[O:11])[C:3]=1[C:4]#[N:5].[NH4+:21].[OH-]>CO.CCO>[NH2:21][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)(=[O:12])=[O:11])[C:3]=1[C:4]#[N:5] |f:1.2,3.4| | FC1=C(C#N)C(=CC=C1)S(=O)(=O)C1=CC(=CC=C1)OC.[NH4+].[OH-] | 2-fluoro-6-[(3-methoxyphenyl)sulfonyl]benzonitrile;NH4OH | 0.7;20.0 | g;mL | CO.CCO | MeOH EtOH | 110.0 | mL | null | null | null | null | null | null | null | null | 130.0 | null | NC1=C(C#N)C(=CC=C1)S(=O)(=O)C1=CC(=CC=C1)OC | 2-Amino-6-[(3-methoxyphenyl)sulfonyl]benzonitrile | null | null | null |
ord-f52f628e55bf48349560d5f7350120df | [F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[C:3]=1[C:4]#[N:5].ClC1C=CC=C(C(OO)=[O:27])C=1.S(=O)(O)[O-].[Na+]>O>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=[O:27])[C:3]=1[C:4]#[N:5] |f:2.3| | ClC1=CC(=CC=C1)C(=O)OO.S([O-])(O)=O.[Na+]..FC1=C(C#N)C(=CC=C1)SC1=CC(=CC=C1)OC.ClC1=CC(=CC=C1)C(=O)OO. | m-chloroperbenzoic acid;sodium bisulfite;resultant mixture;2-fluoro-6-[(3-methoxyphenyl)thio]benzonitrile;m-chloroperbenzoic acid;resultant mixture | 0.16;0.0;0.0;2.0;1.6;0.0 | g;mol;mol;g;g;mol | O | water | 0.0 | mol | null | null | null | null | null | null | null | null | null | null | FC1=C(C#N)C(=CC=C1)S(=O)C1=CC(=CC=C1)OC | 2-Fluoro-6-[(3-methoxyphenyl)sulfinyl]benzonitrile | null | null | null |
ord-efbec65196ea4c25a91fe4f5f0f30b06 | F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)=[O:11])[C:3]=1[C:4]#[N:5].[NH4+:20].[OH-]>CO.CCO>[NH2:20][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)=[O:11])[C:3]=1[C:4]#[N:5] |f:1.2,3.4| | FC1=C(C#N)C(=CC=C1)S(=O)C1=CC(=CC=C1)OC.[NH4+].[OH-] | 2-fluoro-6-[(3-methoxyphenyl)sulfinyl]benzonitrile;NH4OH | 0.73;20.0 | g;mL | CO.CCO | MeOH EtOH | 65.0 | mL | null | null | null | null | null | null | null | null | 130.0 | null | NC1=C(C#N)C(=CC=C1)S(=O)C1=CC(=CC=C1)OC | 2-Amino-6-[(3-methoxyphenyl)sulfinyl]benzonitrile | null | null | null |
ord-6ddfb59c25f34fe781aa3d4f78fc3efa | [CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:11]=2[C:12]#[N:13])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[OH:19]OS([O-])=O.[K+]>CO.O>[CH3:8][C:6]1[CH:5]=[C:4]([S:9]([C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:11]=2[C:12]#[N:13])=[O:19])[CH:3]=[C:2]([CH3:1])[CH:7]=1 |f:1.2| | CC=1C=C(C=C(C1)C)SC1=C(C#N)C(=CC=C1)F.OOS(=O)[O-].[K+] | 2-[(3,5-Dimethylphenyl)thio]-6-fluorobenzonitrile;OXONE | 1.0;0.0 | g;mol | O.CO | water;methanol | 15.0;100.0 | mL;mL | null | null | null | null | null | null | null | null | null | null | CC=1C=C(C=C(C1)C)S(=O)C1=C(C#N)C(=CC=C1)F | 2-[(3,5-dimethylphenyl)sulfinyl]-6-fluorobenzonitrile | 0.5 | g | 47 |
ord-3a63765ce57f4be88697886cd8f75569 | [CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:11]=2[C:12]#[N:13])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[OH:19]OS([O-])=O.[K+].[OH2:25]>CO>[CH3:8][C:6]1[CH:5]=[C:4]([S:9]([C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:11]=2[C:12]#[N:13])(=[O:19])=[O:25])[CH:3]=[C:2]([CH3:1])[CH:7]=1 |f:1.2| | O.OOS(=O)[O-].[K+].CC=1C=C(C=C(C1)C)SC1=C(C#N)C(=CC=C1)F.OOS(=O)[O-].[K+] | water;OXONE;2-[(3,5-Dimethylphenyl)thio]-6-fluorobenzonitrile;OXONE | 30.0;0.0;1.0;0.0 | mL;mol;g;mol | CO | methanol | 100.0 | mL | null | null | null | null | null | null | null | null | null | null | CC=1C=C(C=C(C1)C)S(=O)(=O)C1=C(C#N)C(=CC=C1)F | 2-[(3,5-dimethylphenyl)sulfonyl]-6-fluorobenzonitrile | 0.73 | g | 65 |
ord-ba9711ed922e47f3840d3a080575bd49 | [CH3:1][C:2]1[CH:3]=[C:4]([S:9]([C:11]2[CH:18]=[CH:17][CH:16]=[C:15](F)[C:12]=2[C:13]#[N:14])=[O:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[NH3:20].CCOC(C)=O>CO>[NH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[C:11]([S:9]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=2)=[O:10])[C:12]=1[C:13]#[N:14] | CCOC(=O)C.CC=1C=C(C=C(C1)C)S(=O)C1=C(C#N)C(=CC=C1)F.N | EtOAc;2-[(3,5-Dimethylphenyl)sulfinyl]-6-fluorobenzonitrile;ammonia | 0.0;0.4;20.0 | mol;g;mL | CO | methanol | 40.0 | mL | null | null | null | null | null | null | null | null | -78.0 | null | NC1=C(C#N)C(=CC=C1)S(=O)C1=CC(=CC(=C1)C)C | 2-amino-6-[(3,5-dimethylphenyl)sulfinyl]benzonitrile | 0.24 | g | 59.2 |
ord-b5f73f3ea0a54afca47617c9e6b59c43 | [CH3:1][C:2]1[CH:3]=[C:4]([S:9]([C:12]2[CH:19]=[CH:18][CH:17]=[C:16](F)[C:13]=2[C:14]#[N:15])(=[O:11])=[O:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[NH3:21].CCOC(C)=O>CO>[NH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[C:12]([S:9]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=2)(=[O:11])=[O:10])[C:13]=1[C:14]#[N:15] | CCOC(=O)C.CC=1C=C(C=C(C1)C)S(=O)(=O)C1=C(C#N)C(=CC=C1)F.N | EtOAc;2-[(3,5-Dimethylphenyl)sulfonyl]-6-fluorobenzonitrile;ammonia | 0.0;0.5;20.0 | mol;g;mL | CO | methanol | 80.0 | mL | null | null | null | null | null | null | null | null | -78.0 | 24 | NC1=C(C#N)C(=CC=C1)S(=O)(=O)C1=CC(=CC(=C1)C)C | 2-amino-6-[(3,5-dimethylphenyl)sulfonyl]benzonitrile | 0.28 | g | 57.5 |
ord-6c9f5721435e410ba7c84870a32cbc44 | Br[C:2]1[CH:3]=[C:4]([CH3:10])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[Li]C(CC)C.[S].[F:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22](F)[C:19]=1[C:20]#[N:21].C[S:28](C)=O>C(=O)=O.CC(C)=O.O.C1COCC1>[F:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([S:28][C:2]2[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[CH:3]=2)[C:19]=1[C:20]#[N:21] ... | FC1=C(C#N)C(=CC=C1)F.CS(=O)C.BrC=1C=C(C=C(C1)OC)C.[Li]C(C)CC..[S] | 2,6-difluorobenzonitrile;DMSO;3-bromo-5-methoxytoluene;sec-BuLi;resultant mixture;sulfur | 0.69;5.0;1.0;8.46;0.0;0.19 | g;mL;g;mL;mol;g | .C(=O)=O.CC(=O)C.C1CCOC1.O | ice water;dry ice acetone;THF;water | 0.0;0.0;0.0;100.0 | mol;mol;mol;mL | null | null | null | null | null | null | null | null | null | 0.3333 | FC1=C(C#N)C(=CC=C1)SC1=CC(=CC(=C1)OC)C | 2-Fluoro-6-[(3 -methyl-5-methoxyphenyl)thio]benzonitrile | null | null | null |
ord-1a88c0d5212446d3b4c2d1662ded1557 | F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([CH3:19])[CH:12]=2)[C:3]=1[C:4]#[N:5].[NH3:20]>C(O)C.C1COCC1>[NH2:20][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([CH3:19])[CH:12]=2)[C:3]=1[C:4]#[N:5] | FC1=C(C#N)C(=CC=C1)SC1=CC(=CC(=C1)OC)C.N. | 2-fluoro-6-[(3-methyl-5-methoxyphenyl)thio]benzonitrile;ammonia;resultant solution | 0.1;0.0;0.0 | g;mol;mol | C(C)O.C1CCOC1 | ethanol;THF | 10.0;2.0 | mL;mL | null | null | null | null | null | null | null | null | 145.0 | null | NC1=C(C#N)C(=CC=C1)SC1=CC(=CC(=C1)OC)C | 2-Amino-6-[(3 -methyl-5-methoxyphenyl)thio]benzonitrile | null | null | null |
ord-b52dd58a1564476b8012385c8b071efd | F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([CH3:21])[CH:14]=2)(=[O:12])=[O:11])[C:3]=1[C:4]#[N:5].[NH3:22]>C(O)C.C1COCC1>[NH2:22][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([CH3:21])[CH:14]=2)(=[O:12])=[O:11])[C:3]=1[C:4]#[N... | FC1=C(C#N)C(=CC=C1)S(=O)(=O)C1=CC(=CC(=C1)OC)C.N. | 2-fluoro-6-[(3-methyl-5-methoxyphenyl)sulfonyl]benzonitrile;ammonia;resultant solution | 0.3;0.0;0.0 | g;mol;mol | C(C)O.C1CCOC1 | ethanol;THF | 10.0;2.0 | mL;mL | null | null | null | null | null | null | null | null | 130.0 | null | NC1=C(C#N)C(=CC=C1)S(=O)(=O)C1=CC(=CC(=C1)OC)C | 2-amino-6-[(3-methyl-5-methoxyphenyl)sulfonyl]benzonitrile | 0.1 | g | 34 |
ord-57d496f8cfa74e14b0b60ed9b08a5969 | [NH2:1][CH:2]([CH2:6][CH3:7])[C:3]([OH:5])=[O:4].S(Cl)([Cl:10])=O.[CH2:12](OCC)[CH3:13]>C(O)C>[ClH:10].[NH2:1][CH:2]([CH2:6][CH3:7])[C:3]([O:5][CH2:12][CH3:13])=[O:4] |f:4.5| | NC(C(=O)O)CC.S(=O)(Cl)Cl.C(C)OCC | 2-aminobutyric acid;thionyl chloride;diethyl ether | 100.0;120.8;600.0 | g;g;mL | C(C)O | ethanol | 300.0 | mL | null | null | null | null | null | null | null | null | 0.0 | 8 | Cl.NC(C(=O)OCC)CC | desired product | 150 | g | null |
ord-968da5d345074707bd8ae7f036b4987e | Cl.[NH2:2][CH:3]([CH2:9][CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].S([O-])([O-])(=O)=O.[Mg+2].C(N(CC)CC)C.[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl>[CH:24](=[N:2][CH:3]([CH2:9][CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1 |f:0.1,2.3| | C(C1=CC=CC=C1)=O.Cl.NC(C(=O)OCC)CC.S(=O)(=O)([O-])[O-].[Mg+2].C(C)N(CC)CC | benzaldehyde;product;magnesium sulphate;triethylamine | 94.9;149.6;74.3;246.0 | g;g;g;mL | ClCCl | dichloromethane | 1500.0 | mL | null | null | null | null | null | null | null | null | ambient | 3 | C(C1=CC=CC=C1)=NC(C(=O)OCC)CC | desired product | 174 | g | 88.9 |
ord-8bc8a5b260b5493c8773ed6d142bea7c | [NH2:1][C:2]([CH2:12][CH3:13])([CH2:8][CH:9]=[CH:10][CH3:11])[C:3](OCC)=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[NH2:1][C:2]([CH2:12][CH3:13])([CH2:8][CH:9]=[CH:10][CH3:11])[CH2:3][OH:4] |f:1.2.3.4.5.6,7.8| | [OH-].[Na+].NC(C(=O)OCC)(CC=CC)CC..[H-].[Al+3].[Li+].[H-].[H-].[H-] | NaOH;product;solution;lithium aluminium hydride | 200.0;116.7;0.0;0.0 | mL;g;mol;mol | C1CCOC1.C1CCOC1 | THF;THF | 100.0;800.0 | mL;mL | null | null | null | null | null | null | null | null | ambient | 8 | NC(CO)(CC=CC)CC | desired product | 29.3 | g | 32.5 |
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