Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [OH:1][C:2]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][C:5]([CH2:6][NH:7][N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:4][C:3]=1[C:19]([CH3:22])([CH3:21])[CH3:20].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(O)(=O)C.C1C=CC=CC=1>[OH:1][C:2]1[C:14]([C:15]([CH3:17])([CH3:16])[CH3:18])=[CH:13][C:5]([CH:6]=[N:7][N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:4][C:3]=1[C:19]([CH3:22])([CH3:21])[CH3:20]
Reactant: CC(C)(C)c1cc(CNn2ccnc2)cc(C(C)(C)C)c1O
Agent: N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O
Solvent: CC(=O)O
Solvent: c1ccccc1
Product: CC(C)(C)c1cc(C=Nn2ccnc2)cc(C(C)(C)C)c1O

Procedure:
300 mg of 1-(4-hydroxy-3,5-di-tert.-butylbenzylamino)imidazole are heated to about 60°-70° on a water-bath together with 10 drops of glacial acetic acid in 25 ml of benzene. After the dropwise addition of a solution of 250 mg of dicyanodichlorobenzoquinone in 10 ml of benzene, the mixture is warmed for an additional 15 minutes. The reaction mixture is subsequently cooled in an ice-bath and the separated solid is removed by filtration. The filtrate is shaken with 10% sodium carbonate solution. After separation of the organic phase the aqueous phase is extracted once with benzene. The combined organic phases are dried with anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The crystalline residue is recrystallized from ethyl acetate/n-hexane and there is obtained 1-(4-hydroxy-3,5-di-tert.-butylbenzylideneamino)imidazole of m.p. 173°.
Reaction SMILES: [N:1]([C:4]1[C:9]([F:10])=[C:8]([Cl:11])[CH:7]=[CH:6][C:5]=1[F:12])=[N+:2]=[N-:3].Cl[C:14]1C(F)=C(C(F)=C[CH:20]=1)N.N([O-])=O.[Na+].[N-]=[N+]=[N-].[Na+].[C:31]([OH:37])([C:33](F)(F)F)=[O:32]>O>[Cl:11][C:8]1[C:9]([F:10])=[C:4]([N:1]2[C:14]([CH3:20])=[C:33]([C:31]([OH:37])=[O:32])[N:3]=[N:2]2)[C:5]([F:12])=[CH:6][CH:7]=1
Reactant: O=C(O)C(F)(F)F
Reactant: [N-]=[N+]=Nc1c(F)ccc(Cl)c1F
Reactant: Nc1c(F)ccc(Cl)c1F
Agent: O=N[O-]
Agent: [N-]=[N+]=[N-]
Agent: [Na+]
Solvent: O
Product: Cc1c(C(=O)O)nnn1-c1c(F)ccc(Cl)c1F
Temperature: 0 °C
Reaction time: 0.17 h
Yield: 56 %

Procedure:
2-Azido-4-chloro-1,3-difluorobenzene: To a solution of 3-chloro-2,6-difluoroaniline (1.7 g, 10.39 mmol) in TFA (10 mL) and water (2 mL) at 0° C. was added sodium nitrite (0.717 g, 10.39 mmol) over a period of 0.5 h. After completion of addition, sodium azide (1.716 g, 26.4 mmol) in water (5 mL) was added dropwise. The reaction mixture was stirred at 0° C. for 10 min and then allowed to warm to rt. The reaction was diluted with water (75 mL) and extracted with EtOAc. The organic layer was dried and concentrated to give the desired product (1.16 g, 56%) as a brown solid.
Reaction SMILES: [Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([C:12](=O)[CH2:13][C:14](=O)[CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])=[C:4]([F:24])[CH:3]=1.O.[NH2:26][NH2:27]>C(O)C>[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([C:12]2[CH:13]=[C:14]([CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])[NH:27][N:26]=2)=[C:4]([F:24])[CH:3]=1
Reactant: CCOC(OCC)C(=O)CC(=O)c1cc(OC(C)C)c(Cl)cc1F
Reactant: NN
Solvent: CCO
Solvent: O
Product: CCOC(OCC)c1cc(-c2cc(OC(C)C)c(Cl)cc2F)n[nH]1

Procedure:
The crude 1-(4-chloro-2-fluoro-5-isopropoxy-phenyl)-4,4-diethoxybutane-1,3-dione (Example H7) is initially introduced into 150 ml of dry ethanol. 2.90 g of hydrazine monohydrate are added dropwise at room temperature, while stirring. The mixture is then stirred for 4 hours, while heating under gentle reflux, and is subsequently cooled and the alcohol is removed on a rotary evaporator in vacuo. The residue obtained is partitioned between aqueous sodium bicarbonate solution and ethyl acetate. After extraction by shaking and separation of the phases, the organic phase is washed with water and then dried over sodium sulfate and concentrated. 17.5 g of a dark yellow oil are obtained.
Reaction SMILES: C([Li])CCC.[CH3:6][O:7][CH:8]([O:23][CH3:24])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[C:10]=1[O:19][CH2:20][O:21][CH3:22].CN(C)CCN(C)C.CN(C)[CH:35]=[O:36].Cl>C(OCC)C>[CH3:6][O:7][CH:8]([O:23][CH3:24])[C:9]1[C:10]([O:19][CH2:20][O:21][CH3:22])=[C:11]([C:15]([F:17])([F:18])[F:16])[CH:12]=[CH:13][C:14]=1[CH:35]=[O:36]
Reactant: CN(C)C=O
Reactant: COCOc1c(C(OC)OC)cccc1C(F)(F)F
Agent: CN(C)CCN(C)C
Agent: Cl
Agent: [Li]CCCC
Solvent: CCOCC
Product: COCOc1c(C(F)(F)F)ccc(C=O)c1C(OC)OC
Temperature: 0 °C
Reaction time: 0.5 h

Procedure:
A n-butyl lithium-1.59M n-hexane solution (196 ml, 312 mmol) was added dropwise to a solution of 1-(dimethoxymethyl)-2-(methoxymethoxy)-3-(trifluoromethyl)benzene (39.3 g, 140 mmol) obtained in Example (6-4) and N,N,N′,N′-tetramethylethylenediamine (46.9 ml, 311 mmol) in diethyl ether (410 ml) at −25° C. over 20 minutes. After the reaction mixture was stirred at 0° C. for 30 minutes, it was further stirred at room temperature for 1.5 hours. After the reaction mixture was cooled to −30° C. and N,N-dimethylformamide (41.9 ml, 541 mmol) was added thereto, the mixture was further stirred at room temperature for 1 hour. After the reaction mixture was carefully poured into cold 0.1N hydrochloric acid and the mixture was extracted with ethyl acetate (four times), the organic layer was successively washed with 0.1N hydrochloric acid, water (three times) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to give crude 2-(dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)benzaldehyde. This compound was used in Example (6-6) without further purification.
Reaction SMILES: [N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[NH:15][CH2:14][CH2:13][N:12]=2)[CH:2]=1.[C:22](OC(=O)C)(=[O:24])[CH3:23].N1C=CC=CC=1.C(OCC)(=O)C>C(Cl)Cl>[C:22]([N:15]1[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:11]([C:3]2[CH:2]=[N:1][C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)=[N:12][CH2:13][CH2:14]1)(=[O:24])[CH3:23]
Reactant: CC(=O)OC(C)=O
Reactant: c1ccc2c(c1)NCCN=C2c1cnc2ccccc2c1
Solvent: ClCCl
Solvent: c1ccncc1
Solvent: CCOC(C)=O
Product: CC(=O)N1CCN=C(c2cnc3ccccc3c2)c2ccccc21
Temperature: 25 °C
Reaction time: 2 h
Yield: 73.8 %

Procedure:
2,3-Dihydro-5-(3-quinolinyl)-1H-1,4-benzodiazepine (0.20 g, 0.73 mmol) was dissolved in 10 mL of methylene chloride, and acetic anhydride (0.1 mL, 1.1 mmol), pyridine (0.18 mL, 2.2 mmol) were added to the resulting solution, followed by stirring at room temperature for 2 hours. Then the resulting solution was distilled off under redused pressure for 14 hours. The resulting reaction solution was cooled to room temperature and added with ethyl acetate. Then the solution was washed with 0.5N citric acid solution, brine and saturated bicarbonate water, followed by drying with magnesium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform:methanol=9:1) to obtain the target compound (0.17 g, yield: 15%).
Reaction SMILES: FC(F)(F)C(O)=O.[F:8][C:9]1[CH:14]=[C:13]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:12]=[CH:11][C:10]=1[C:19]1[NH:23][C:22]2[CH:24]=[CH:25][C:26]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[CH:27][C:21]=2[N:20]=1.Cl[C:35]1[N:40]=[CH:39][C:38]([CH2:41][CH3:42])=[CH:37][N:36]=1.CCN(C(C)C)C(C)C>CC(O)C>[CH2:41]([C:38]1[CH:37]=[N:36][C:35]([N:31]2[CH2:32][CH2:33][CH:28]([C:26]3[CH:25]=[CH:24][C:22]4[NH:23][C:19]([C:10]5[CH:11]=[CH:12][C:13]([S:15]([CH3:18])(=[O:16])=[O:17])=[CH:14][C:9]=5[F:8])=[N:20][C:21]=4[CH:27]=3)[CH2:29][CH2:30]2)=[N:40][CH:39]=1)[CH3:42]
Reactant: CS(=O)(=O)c1ccc(-c2nc3cc(C4CCNCC4)ccc3[nH]2)c(F)c1
Reactant: CCc1cnc(Cl)nc1
Solvent: CC(C)O
Solvent: O=C(O)C(F)(F)F
Solvent: CCN(C(C)C)C(C)C
Product: CCc1cnc(N2CCC(c3ccc4[nH]c(-c5ccc(S(C)(=O)=O)cc5F)nc4c3)CC2)nc1
Temperature: 90 °C
Reaction time: 12 h
Yield: 26.1 %

Procedure:
Example 57 (150 mg, 0.3 mmol) dissolved in DCM (12 ml) and added TFA (0.45 ml). This mixture stirred at rt for 3 h. After 3 h, DCM removed on rotavapour and co-distilled with DCM to obtain 2-[2-fluoro-4-(methylsulfonyl)phenyl]-5-(piperidin-4-yl)-1H-benzo[d]imidazole 2,2,2-trifluoroacetate (150 mg). 2-[2-fluoro-4-(methylsulfonyl)phenyl]-5-(piperidin-4-yl)-1H-benzo[d]imidazole 2,2,2-trifluoroacetate (150 mg, 0.4 mmol) and 2-chloro-5-ethylpyrimidine (60 mg, 0.4 mmol) were dissolved in propan-2-ol (10 ml) and added DiPEA (0.6 ml, 3.2 mmol). This mixture was refluxed at 90° C. for 12 h. After 12 h, propan-2-ol removed on rotavapor to obtain the residue. Residue was purified on combiflash using Ethyl acetate and Petether (1:1) as eluent to afford the titled compound (50 mg) as a white solid. M.P.: 220-223.5° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 12.69 (d, J 12.8, 1H), 8.49-8.45 (m, 1H), 8.24 (s, 2H), 8.00 (dd, J 1.5, 10.4, 1H), 7.91 (d, J 8.3, 1H), 7.67-7.56 (m, 1H), 7.55-7.40 (m, 1H), 7.22-7.12 (m, 1H), 4.80 (d, J 12.6, 2H), 3.33 (s, 3H), 2.97-2.91 (m, 3H), 2.43 (q, J 7.5, 2H), 1.89 (d, J 12.4, 2H), 1.69-1.54 (m, 2H), 1.13 (t, J 7.6, 3H).
Reaction SMILES: [CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][Cl:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]1([P:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[Cl-:16].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][P+:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
Reactant: ClCc1ccc(OCc2ccccc2)cc1
Reactant: c1ccc(P(c2ccccc2)c2ccccc2)cc1
Solvent: Cc1ccccc1
Product: [Cl-]
Product: c1ccc(COc2ccc(C[P+](c3ccccc3)(c3ccccc3)c3ccccc3)cc2)cc1
Temperature: 25 °C
Yield: 88.1 %

Procedure:
To a suspension of 1-(benzyloxy)-4-(chloromethyl)benzene (4.890 g, 21.01 mmol) in toluene (25 ml) was added triphenylphosphine (6.617 g, 25.23 mmol). The mixture was heated under reflux for 24 hrs, and cooled to room temperature. The precipitate was collected by filtration, and dried under reduced pressure to give [4-(benzyloxy)benzyl](triphenyl)phosphonium chloride (9.166 g, yield 88.1%) as a white solid.
Reaction SMILES: [OH:1][CH:2]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[C:26](O)(=[O:42])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>>[C:26]([O:1][CH:2]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:3][C:4]([O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:5])(=[O:42])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]
Reactant: CCCCCCCCCCCCCCCC(O)CC(=O)OC(C)(C)C
Reactant: CCCCCCCCCCCCCCCC(=O)O
Product: CCCCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCCCCCC)CC(=O)OC(C)(C)C
Yield: 96.5 %

Procedure:
tert-Butyl 3-hydroxyoctadecanoate (1.068 g) was acylated by the acid chloride derived from hexadecanoic acid (3.84 g) according to similar manner to that of Preparation 1-(2) to give an oil of tert-butyl 3-hexadecanoyloxyoctadecanoate (1.72 g).
Reaction SMILES: Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][C:9](Br)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[CH:19]1([Mg]Br)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.Cl>C1COCC1.O1CCOCC1>[CH:19]1([C:2]2[C:15]3[C:16]4=[C:17]5[C:12](=[CH:13][CH:14]=3)[CH:11]=[CH:10][C:9]([CH:2]3[CH2:15][CH2:16][CH2:5][CH2:4][CH2:3]3)=[C:8]5[CH:7]=[CH:6][C:5]4=[CH:4][CH:3]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1
Reactant: Br[Mg]C1CCCCC1
Reactant: Brc1ccc2ccc3c(Br)ccc4ccc1c2c43
Agent: Cl
Solvent: C1COCCO1
Solvent: C1CCOC1
Product: c1cc2ccc3c(C4CCCCC4)ccc4ccc(c1C1CCCCC1)c2c43
Temperature: 90 °C
Yield: 71 %

Procedure:
Under an atmospheric argon gas flow, 1,6-dibromopyrene in an amount of 20 g (55.6 millimole), cyclohexylmagnesiumbromide in an amount of 117 milliliter [117 millimole, 1 mole/liter (THF: tetrahydrofuran)], (diphenylphosphinoferrocene)palladium(II)dichloride in an amount of 2.27 g (5% by mole), dried dioxane in an amount of 80 milliliter and THF in an amount of 70 milliliter were placed into a three-neck flask equipped with a cooling pipe and having a capacity of 500 milliliter, and the resultant solution was stirred with heating at a temperature of 90° C. for 8 hours. After the completion of the reaction, adding 100 milliliter of dilute hydrochloric acid, an organic layer was separated and concentrated under a reduced pressure. Then, the organic layer was passed through a silicagel short column, and after concentrating under the reduced pressure again, a precipitated crystal was separated by filtration and as a result, 7.0 g of 1,6-dicyclohexylpyrene (pale yellow powder) was obtained (the yield: 71%).
Reaction SMILES: C([Li])CCC.[C:6]([O:9][CH2:10][CH3:11])(=[O:8])[CH3:7].[C:12]([C:14]1[CH:34]=[CH:33][C:17]2[O:18][C:19]([CH3:32])([CH3:31])[CH:20]=[C:21]([N:22]3[CH:27]=[CH:26][C:25]([CH:28]=[O:29])=[CH:24][C:23]3=[O:30])[C:16]=2[CH:15]=1)#[N:13].P([O-])([O-])([O-])=O>O1CCCC1.C(NC(C)C)(C)C.CCCCCC>[C:12]([C:14]1[CH:34]=[CH:33][C:17]2[O:18][C:19]([CH3:31])([CH3:32])[CH:20]=[C:21]([N:22]3[CH:27]=[CH:26][C:25]([CH:28]([OH:29])[CH2:7][C:6]([O:9][CH2:10][CH3:11])=[O:8])=[CH:24][C:23]3=[O:30])[C:16]=2[CH:15]=1)#[N:13]
Reactant: CCOC(C)=O
Reactant: CC1(C)C=C(n2ccc(C=O)cc2=O)c2cc(C#N)ccc2O1
Agent: O=P([O-])([O-])[O-]
Agent: [Li]CCCC
Solvent: CCCCCC
Solvent: CC(C)NC(C)C
Solvent: C1CCOC1
Product: CCOC(=O)CC(O)c1ccn(C2=CC(C)(C)Oc3ccc(C#N)cc32)c(=O)c1
Temperature: 0 °C
Reaction time: 0.17 h

Procedure:
In 40 ml of anhydrous tetrahydrofuran, is dissolved 3.64 ml of diisopropylamine. The resulting solution is cooled to 0° C. After dropping 15.4 ml of 1.62M solution of n-butyllithium in n-hexane thereto and stirring the resulting mixture for 10 minutes at that temperature, it is cooled to -78° C. and stirred for 20 minutes. Then, 2.34 ml of ethyl acetate is dropped and stirred at that temperature for 30 minutes. Then, 160 ml of an anhydrous tetrahydrofuran solution containing 6.13 g of the 6-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-formyl-1-pyridinyl)-2H-benzo[b]pyran obtained in Example 25 is added at that temperature over a period of 55 minutes, and the whole mixture is reacted first at that temperature for one hour, then at 0° C. for 30 minutes and then at room temperature for 30 minutes. After stopping the reaction by adding 0.2M phosphate buffer, the reaction mixture is extracted with ethyl acetate. The organic layer is washed successively with 2N aqueous hydrochloric acid, water and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The inorganic matter is filtered off, and the filtrate is concentrated under reduced pressure. The residue thus obtained is purified by silica gel column chromatography using 3/1 mixture of ethyl acetate/n-hexane as a developing solvent. Thus, 5.88 g of 6-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(1-hydroxy-2- ethoxycarbonylethyl)- 1-pyridinyl}-2H-benzo[b]pyran is obtained.
Reaction SMILES: [CH2:1]([Li])CCC.[CH3:6][C:7]([CH3:23])([C:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH3:6][C:7]([CH3:23])([C:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH2:1])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]
Reactant: CC(C)(C)OC(=O)C(C)(C)C(=O)c1ccccc1
Reactant: [Li]CCCC
Agent: C[P+](c1ccccc1)(c1ccccc1)c1ccccc1
Agent: [Br-]
Solvent: C1CCOC1
Product: C=C(c1ccccc1)C(C)(C)C(=O)OC(C)(C)C

Procedure:
After methyltriphenylphosphonium bromide and n-butyllithium were reacted in THF, a THF solution of tert-butyl 2,2-dimethyl-3-oxo-3-phenylpropanoate was added thereto and the whole was reacted under heating to obtain tert-butyl 2,2-dimethyl-3-phenylbut-3-enoate.
Reaction SMILES: CN(C)C=O.Cl[C:7]([O:9][CH2:10][CH3:11])=[O:8].[O:12]=[C:13]1[N:18]2[C:19]3[C:24]([NH:25][CH2:26][C:17]2=[N:16][CH:15]=[C:14]1[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:23][CH:22]=[CH:21][CH:20]=3>O>[O:12]=[C:13]1[N:18]2[C:19]3[C:24]([N:25]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:26][C:17]2=[N:16][CH:15]=[C:14]1[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:23][CH:22]=[CH:21][CH:20]=3
Reactant: CCOC(=O)c1cnc2n(c1=O)-c1ccccc1NC2
Reactant: CCOC(=O)Cl
Solvent: O
Solvent: CN(C)C=O
Product: CCOC(=O)c1cnc2n(c1=O)-c1ccccc1N(C(=O)OCC)C2
Reaction time: 8 h
Yield: 39.5 %

Procedure:
4 ml of dry dimethylformamide were saturated with nitrogen for 10 minutes before 150 mg of ethyl chloroformate and 280 mg of ethyl 5,6-dihydro-1-oxo-1H-pyrimido [1,2-a] quinoxaline-2-carboxylate were added thereto. The solution obtained was left at room temperature overnight and then was poured into water. The mixture was extracted with ethyl acetate and the organic phase was dried over MgSO4 and evaporated to dryness. The residue was chromatographed over silica gel and eluted with ethyl acetate to obtain 140 mg (41% yield) of diethyl 5,6-dihydro-1-oxo-1H-pyrimido [1,2-a] quinoxaline-2,6-dicarboxylate melting at 140°-2° C.
Reaction SMILES: [CH2:1]([O:3][C:4]1[CH:26]=[CH:25][CH:24]=[CH:23][C:5]=1[O:6][S:7]([NH:10][C:11](=[O:22])OC1C=CC=CC=1OCC)(=[O:9])=[O:8])[CH3:2].[NH2:27][C:28]1[N:33]=[C:32]([O:34][CH3:35])[CH:31]=[C:30]([O:36][CH3:37])[N:29]=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:26]=[CH:25][CH:24]=[CH:23][C:5]=1[O:6][S:7]([NH:10][C:11]([NH:27][C:28]1[N:29]=[C:30]([O:36][CH3:37])[CH:31]=[C:32]([O:34][CH3:35])[N:33]=1)=[O:22])(=[O:8])=[O:9])[CH3:2]
Reactant: COc1cc(OC)nc(N)n1
Reactant: CCOc1ccccc1OC(=O)NS(=O)(=O)Oc1ccccc1OCC
Solvent: Cc1ccccc1
Product: CCOc1ccccc1OS(=O)(=O)NC(=O)Nc1nc(OC)cc(OC)n1
Temperature: 100 °C
Yield: 97.5 %

Procedure:
38.1 g of 2-ethoxyphenyl N-(2-ethoxyphenoxysulfonyl)carbamate are dissolved in 500 ml of toluene, 15.5 g of 2-amino-4,6-dimethoxypyrimidine are added at room temperature, and the mixture is heated for 2 hours at 100° C. After cooling to 30° C., the precipitate is filtered off and washed with 100 ml of toluene. 38.8 g of the desired product are obtained with a purity of 98.8%, corresponding to a yield of 96.4% of theory. The melting point for the product is 147°-149° C. 6.5 g of 2-ethoxyphenol are recovered from the mother liquor by distillation.
Reaction SMILES: [CH2:1]([NH:8][C:9]1[S:10][C:11]([CH3:17])=[C:12]([CH3:16])[C:13]=1[C:14]#[N:15])[C:2]1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].C(I)C>C(#N)C.C(OCC)(=O)C>[CH2:1]([NH:8][C:9]1[S:10][C:11]([CH3:17])=[C:12]([CH3:16])[C:13]=1[C:14]#[N:15])[CH3:2]
Reactant: Cc1sc(NCc2ccccc2)c(C#N)c1C
Agent: O=C([O-])[O-]
Agent: [I-]
Agent: [K+]
Solvent: CCOC(C)=O
Solvent: CC#N
Solvent: CCI
Product: CCNc1sc(C)c(C)c1C#N
Reaction time: 0.25 h

Procedure:
To a mixture of 2-(benzylamino)-4,5-dimethylthiophene-3-carbonitrile (302 mg, 2.0 mmol), potassium carbonate (276 mg, 2.0 mmol), and a catalytic amount of potassium iodide in acetonitrile (1 mL) in a 20 mL microwave vial was added ethyl iodide (310 mg, 2.0 mmol). The reaction vial was placed in a microwave reactor for 15 minutes at 165° C. The reaction mixture was dissolved in ethyl acetate and washed with water and brine. The ethyl acetate portion was dried over sodium sulfate and solvent was evaporated under reduced pressure, and the product was purified by prep HPLC using acetonitrile/water as solvent. MS 181 (MH+).
Reaction SMILES: I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(NC(C)C)(C)C.[CH3:15][C:16]([CH3:20])([CH3:19])[C:17]#[CH:18]>CN(C)C=O.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:15][C:16]([CH3:20])([CH3:19])[C:17]#[C:18][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
Reactant: C#CC(C)(C)C
Reactant: Ic1ccccc1
Agent: Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1
Agent: [Cu]I
Solvent: CN(C)C=O
Solvent: CC(C)NC(C)C
Solvent: CCOC(C)=O
Product: CC(C)(C)C#Cc1ccccc1
Temperature: 75 °C
Yield: 95.4 %

Procedure:
A degassed solution of iodobenzene (0.549 mL, 4.90 mmol), dichlorobis(triphenylphosphine)-palladium(II) (0.206 g, 0.294 mmol), copper(I) iodide (0.047 g, 0.245 mmol), and diisopropylamine (3.49 mL, 24.5 mmol) in N,N-dimethylformamide (20 mL) was added 3,3-dimethylbut-1-yne (0.896 mL, 7.35 mmol). The reaction mixture was and heated to 75° C. for 45 minutes. The reaction mixture was then diluted with ethyl acetate (150 mL), washed with 10% aqueous solution of lithium chloride (2×100 mL), washed with a 2M aqueous solution of ammonium hydroxide, washed with brine (100 mL), and dried over anhydrous sodium sulfate. Concentration followed by purification on silica gel chromatography with hexanes/dichloromethane (10/1) afforded (3,3-Dimethylbut-1-ynyl)benzene (740 mg). The compound had an HPLC ret. time=3.78 min.−Column: YMC S5 COMBISCREEN® 4.6×50 mm; Gradient time: 4 min; Flow rate=4 ml/min; Solvent A=10% MeOH−90% Water−0.2% H3PO4; Solvent B=90% MeOH−10% water−0.2% H3PO4; Start % B=0; Final % B=100.
Reaction SMILES: [O-2].[O-2].[U+4:3].[N+:4]([O-:7])([OH:6])=[O:5]>>[N+:4]([O-:7])([O-:6])=[O:5].[U+6:3].[N+:4]([O-:7])([O-:6])=[O:5].[N+:4]([O-:7])([O-:6])=[O:5].[N+:4]([O-:7])([O-:6])=[O:5].[N+:4]([O-:7])([O-:6])=[O:5].[N+:4]([O-:7])([O-:6])=[O:5]
Reactant: O=[N+]([O-])O
Reactant: [U+4]
Agent: [O-2]
Product: O=[N+]([O-])[O-]
Product: [U+6]

Procedure:
In the production of uranium dioxide nuclear fuel pellets, a substantial quantity of uranium dioxide fuel stock powder and some scrap or broken pellets are routinely recycled for reasons of economy and environmental protection. Recycling of the uranium dioxide materials is carried out by dissolving the solid uranium dioxide material in nitric acid, and thereby forming a solution of soluble uranium nitrate. The pH of a water-diluted solution of the soluble uranium nitrate is reduced to about 5 to about 7 with ammonium hydroxide, and then the uranium is precipitated from the solution by the addition of hydrogen peroxide to produce insoluble uranium peroxide according to the reaction:
Reaction SMILES: [CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([CH3:13])([CH3:12])[NH2:11])=[CH:4][CH:3]=1.FC(F)(F)[C:16]1[CH:17]=[C:18]([C:22]([CH:24]=O)=[O:23])[CH:19]=[CH:20][CH:21]=1.C1(C(C=O)=O)C=CC=CC=1>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH:11][CH2:24][CH:22]([OH:23])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:16][CH:17]=2)([CH3:13])[CH3:12])=[CH:4][CH:3]=1
Reactant: Cc1ccc(CCC(C)(C)N)cc1
Reactant: O=CC(=O)c1cccc(C(F)(F)F)c1
Agent: O=CC(=O)c1ccccc1
Product: Cc1ccc(CCC(C)(C)NCC(O)c2ccccc2)cc1

Procedure:
The title compound was prepared in the manner described in Example 9, replacing 2-(4-methylphenyl)-1,1-dimethylethanamine by 3-(4-methylphenyl)-1,1-dimethylpropanamine and 3-trifluoromethylphenyl glyoxal by phenylglyoxal. The chromatographed material was recrystallised from hexane to give the title compound m.p. 107-110. τ (CDCl3) 8.95 (6H, s), 8.2-8.7 (2H, m), 7.8 (3H, s), 7.3-7.7 (4H, m), 5.7-6.5 (2H, m), 5.5 (1H, t, J=6 Hz), 2.9 (4H, s), 2.7 (4H, m).
Reaction SMILES: [N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[NH:18][C:19](=[O:26])[C:20](=[CH:24][CH:25]=2)[C:21](O)=O)=[CH:13][CH:12]=1)(=[O:10])=[O:9].S(Cl)([Cl:29])=O>CN(C)C=O>[ClH:29].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[NH:18][C:19](=[O:26])[C:20](=[CH:24][CH:25]=2)[CH2:21][Cl:29])=[CH:13][CH:12]=1)(=[O:10])=[O:9]
Reactant: O=C(O)c1ccc(-c2ccc(S(=O)(=O)Nc3ccccn3)cc2)[nH]c1=O
Reactant: O=S(Cl)Cl
Solvent: CN(C)C=O
Product: Cl
Product: O=c1[nH]c(-c2ccc(S(=O)(=O)Nc3ccccn3)cc2)ccc1CCl

Procedure:
From 7.0 g. of 6-[4-(2-pyridylaminosulfonyl)phenyl]-1,2-dihydro-2-oxonicotinic acid in 200 ml. of thionyl chloride, and 1.5 ml. of dimethylformamide, following the procedure of c) above, there is obtained 6-[4-(2-pyridylaminosulfonyl)phenyl]-1,2-dihydro-2-oxonicotinyl chloride hydrochloride.