Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [NH2:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]2[CH:10]=[CH:9][S:8][C:7]=12.[OH-].[Na+].[C:13](Cl)(=[O:25])[O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1>C1COCC1.O>[N+:22]([C:19]1[CH:18]=[CH:17][C:16]([CH2:15][O:14][C:13]([NH:1][CH2:2][C:3]2[N:4]=[CH:5][N:6]3[CH:10]=[CH:9][S:8][C:7]=23)=[O:25])=[CH:21][CH:20]=1)([O-:24])=[O:23]
Reactant: O=C(Cl)OCc1ccc([N+](=O)[O-])cc1
Reactant: NCc1ncn2ccsc12
Agent: [Na+]
Agent: [OH-]
Solvent: O
Solvent: C1CCOC1
Product: O=C(NCc1ncn2ccsc12)OCc1ccc([N+](=O)[O-])cc1
Yield: 68.1 %

Procedure:
7-Aminomethylimidazo[5,1-b]thiazole (1.53 g) was dissolved in 50 ml of THF and 30 ml of water. A 1 N aqueous sodium hydroxide solution (12 ml) and 2.59 g of 4-nitrobenzyl chlorocarbonate were added under ice cooling to the solution. The mixture was allowed to react at the same temperature for 30 min. The reaction solution was extracted with 200 ml of ethyl acetate, followed by washing with 15% brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under the reduced pressure to about 20 ml. The resultant crystal was collected by filtration, washed with 20 ml of ethyl acetate, and dried under the reduced pressure to give 2.26 g of 7-(4-nitrobenzyloxycarbonylamino)methylimidazo-[5,1-b]thiazole.
Reaction SMILES: C([N:8]1[C@H:11]([CH2:12][Cl:13])[C@H:10]([N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])[C:9]1=[O:25])C1C=CC=CC=1.[O-]S(OOS([O-])(=O)=O)(=O)=O.[K+].[K+].O.P(O)([O-])([O-])=O.[K+].[K+]>C(O)(=O)C>[C:15]1(=[O:24])[N:14]([C@H:10]2[C@@H:11]([CH2:12][Cl:13])[NH:8][C:9]2=[O:25])[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]12
Reactant: O=C1[C@@H](N2C(=O)c3ccccc3C2=O)[C@@H](CCl)N1Cc1ccccc1
Agent: O=P([O-])([O-])O
Agent: O=S(=O)([O-])OOS(=O)(=O)[O-]
Agent: [K+]
Solvent: O
Solvent: CC(=O)O
Product: O=C1N[C@H](CCl)[C@@H]1N1C(=O)c2ccccc2C1=O
Temperature: 120 °C
Yield: 40.8 %

Procedure:
A mixture of 17.75 g of the product of Step B, 31 g of potassium peroxodisulfate, 110 ml of water and 160 ml of acetic acid was heated for 25 minutes with strong agitation in an oil bath at 120° C. and was then cooled to room temperature. 50 g of dipotassium phosphate were added to the mixture to adjust the pH to neutrality and was evaporated to dryness under reduced pressure. 250 ml of water and 150 ml of ethyl acetate were added to the residue and after stirring, sodium bicarbonate was added in small quantities until evolution of gas ceased. The mixture was filtered and the filtrate was rinsed with ethyl acetate. The decanted aqueous phase was re-extracted with 50 ml of ethyl acetate and the combined organic phases were dried, filtered, rinsed and evaporated to dryness under reduced pressure. The residue was chromatographed over 200 g of silica gel and eluted with methylene chloride with 25% of ethyl acetate. The rich fractions were recovered and evaporated to dryness. The residue was dissolved in ether, and the solution was rinsed and dried to obtain 5.4 g of cis 3-phthalimido-4-chloromethyl-2-azetidinone.
Reaction SMILES: [N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6](=[O:15])[CH:7]=[CH:8][C:9]2=[O:14])([O-:3])=[O:2].[N+]([C:19]1[CH:20]=C2C(=[CH:27][CH:28]=1)C(=O)C=CC2=O)([O-])=O.C=CC=C.ClC=C(Cl)Cl>O>[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6](=[O:15])[C:7]1[CH2:20][CH2:19][CH2:28][CH2:27][C:8]=1[C:9]2=[O:14])([O-:3])=[O:2]
Reactant: O=C1C=CC(=O)c2c1cccc2[N+](=O)[O-]
Reactant: O=C1C=CC(=O)c2cc([N+](=O)[O-])ccc21
Agent: C=CC=C
Solvent: ClC=C(Cl)Cl
Solvent: O
Product: O=C1C2=C(CCCC2)C(=O)c2c1cccc2[N+](=O)[O-]
Reaction time: 2.5 h
Yield: 88 %

Procedure:
41.3 g of a crude 5-nitronaphthoquinone cake (having a water content of 40 wt% and a dry weight of 24.8 g, and comprised of 75 wt% of 5-nitronaphthoquinone and 15 wt% of 6-nitronaphthoquinone when determined under dried conditions), 13.1 g of 1,3-butadiene and 124 g of trichloroethylene were introduced into an autoclave. The autoclave was hermetically sealed and the reaction was effected at 80°C for 2.5 hours. Then, Example 1 was repeated to obtain 20.7 g of 5-nitrotetrahydroanthraquinone. The yield was 88.0%. The thus obtained 5-nitrotetrahydroanthraquinone was oxidized and reduced in accordance with the standard method to obtain 1-aminoanthraquinone having a purity above 98 wt% and a 2-aminoanthraquinone content of 0.5 wt%.
Reaction SMILES: [CH3:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][N:16]=2)[CH2:11][CH2:10]1.[C:24]([Cl:32])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CCOCC>[ClH:32].[C:24]([N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([CH:12]2[CH2:11][CH2:10][N:9]([CH2:4][CH2:5][C:6]3[CH:7]=[CH:8][CH:3]=[CH:2][CH:1]=3)[CH2:14][CH2:13]2)=[N:16]1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1
Reactant: CCc1ccccc1N1CCC(c2n[nH]c3ccccc23)CC1
Reactant: O=C(Cl)c1ccccc1
Solvent: CCOCC
Product: Cl
Product: O=C(c1ccccc1)n1nc(C2CCN(CCc3ccccc3)CC2)c2ccccc21
Yield: 51 %

Procedure:
A mixture of 1.6 g of 3-(1-pheneth-2-yl-4-piperidinyl)-1H-indazole and 7 ml of benzoyl chloride was heated at 100° for 2 hr. After cooling, ether was added and the solid was collected. The solid was combined with material from a prior experiment and recrystallized from methanol to yield 2.4 g (51%) of product, mp 248°-250° C.
Reaction SMILES: [CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]([CH3:11])[CH3:10])[C:4]=1[N:12]=[C:13]=[S:14])[CH3:2].Cl.C([O:18][C:19](=O)[CH2:20][NH:21][CH3:22])C.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]([CH3:11])[CH3:10])[C:4]=1[N:12]1[C:19](=[O:18])[CH2:20][N:21]([CH3:22])[C:13]1=[S:14])[CH3:2]
Reactant: CCOC(=O)CNC
Reactant: CCc1cccc(C(C)C)c1N=C=S
Agent: Cl
Solvent: ClC(Cl)Cl
Solvent: CCN(CC)CC
Product: CCc1cccc(C(C)C)c1N1C(=O)CN(C)C1=S
Yield: 64.9 %

Procedure:
The title compound was prepared by the procedure described in Example 1 using 10.25 g of 2-ethyl-6-isopropylphenyl-isothiocyanate, 7.68 g of sarcosine ethyl ester hydrochloride, 14.8 g of triethyl amine, and 200 mL of chloroform. Crystallization from diethyl ether/hexane mixture afforded the title compound (8.95 g) as a tan solid, m.p. 132°-134° C. Anal. Calcd. for C15H20N2OS: C, 65.18; H, 7.29; N, 10.13. Found: C, 65.11; H, 7.31; N, 10.05. Mass spectrum (PBEI, M.+) m/z 276.
Reaction SMILES: [N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([NH:9][C:10]([C:12]1[S:13][C:14](Br)=[CH:15][CH:16]=1)=[O:11])[CH2:2]2.[Cl:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([NH:9][C:10]([C:12]1[S:13][C:14]([C:23]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:18])[CH:24]=3)=[CH:15][CH:16]=1)=[O:11])[CH2:2]2
Reactant: OB(O)c1cccc(Cl)c1
Reactant: O=C(N[C@H]1CN2CCC1CC2)c1ccc(Br)s1
Agent: c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
Agent: O=C([O-])[O-]
Agent: [Na+]
Solvent: CCO
Solvent: C1CCOC1
Solvent: O
Product: O=C(N[C@H]1CN2CCC1CC2)c1ccc(-c2cccc(Cl)c2)s1

Procedure:
Prepared by a method analogous to that described in Example 1 from (R)-N-(1-azabicyclo[2.2.2]oct-3-yl)(5-bromothiophene-2-carboxamide) and 3-chlorophenylboronic acid, using tetrakis(triphenylphosphine)palladium(0) and sodium carbonate in a mixture of tetrahydrofuran, ethanol and water. The compound was purified by flash chromatography using a gradient of 5%-20% 3.5M methanolic ammonia/chloroform mixtures as the eluent to give the title compound as a colourless solid; MS (ES+) 347 (MH+).
Reaction SMILES: C([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][CH2:15][C:16]([CH3:19])([CH3:18])[N:17]=2)=[CH:9][C:8]=1[O:20][CH3:21].[CH3:22][S:23]SC.Cl>O1CCCC1>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][CH2:15][C:16]([CH3:18])([CH3:19])[N:17]=2)=[C:9]([S:23][CH3:22])[C:8]=1[O:20][CH3:21]
Reactant: CSSC
Reactant: COc1cc(C2=NC(C)(C)CO2)ccc1Cl
Agent: Cl
Agent: [Li]CCCC
Solvent: C1CCOC1
Product: COc1c(Cl)ccc(C2=NC(C)(C)CO2)c1SC
Temperature: -78 °C
Reaction time: 8 h
Yield: 34.5 %

Procedure:
n-Butyllithium (2.5M in hexane, 54 ml) was added with cooling to a stirred solution of 2-(4-chloro-3-methoxyphenyl)-4,4-dimethyloxazoline (27.0 g) in tetrahydrofuran while maintaining the temperature below 40° C. The mixture was stirred at -78° C. overnight. A solution of dimethyl disulphide (26.5 g) in tetrahydrofuran was added dropwise and the mixture was stirred at -40° C. overnight. After allowing to warm to room temperature the mixture was treated with hydrochloric acid (2M). The organic layer was washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by dry column flash chromatography eluted with a mixture of ethyl acetate and n-hexane to give 2-[4-chloro-3-methoxy-2-(methylsulphenyl)-phenyl]4,4-dimethyloxazoline (11.1 g) as a white solid, m.p. 50°-52° C.
Reaction SMILES: [NH2:1][C:2]1[C:29]([Cl:30])=[CH:28][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH2:12][CH2:11]2)=[O:7])=[C:4]([O:31][CH3:32])[CH:3]=1.[CH:33](=O)[CH3:34].C([BH3-])#N.[Na+]>>[NH2:1][C:2]1[C:29]([Cl:30])=[CH:28][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:33][CH3:34])[CH:22]3[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]3)[CH2:12][CH2:11]2)=[O:7])=[C:4]([O:31][CH3:32])[CH:3]=1
Reactant: CC=O
Reactant: COc1cc(N)c(Cl)cc1C(=O)NCC1CCN(CCCCCNC2CCCCC2)CC1
Agent: [BH3-]C#N
Agent: [Na+]
Product: CCN(CCCCCN1CCC(CNC(=O)c2cc(Cl)c(N)cc2OC)CC1)C1CCCCC1

Procedure:
4-Amino-5-chloro-N-((1-(5-cyclohexylaminopentyl)piperidin-4-yl)-methyl)-2-methoxybenzamide (1.1 g) as starting compound, acetaldehyde (0.15 ml) and sodium cyanoborohydride (0.33 g) were reacted and treated in the same manner as in Example 136 to give 1.0 g of 4-amino-5-chloro-N-((1-(5-(N-ethyl-N-cyclohexylamino)pentyl)piperidin-4-yl)methyl)-2-methoxybenzamide.
Reaction SMILES: [NH:1]([C:30]([O:32][CH2:33][CH:34]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:40]2[C:35]1=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:31])[C@H:2]([C:27]([OH:29])=[O:28])[CH2:3][CH2:4][C:5](=[O:26])[NH:6][C:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(OC(C)C)(C)C.[F:54][C:55]1[C:60](O)=[C:59]([F:62])[C:58]([F:63])=[C:57]([F:64])[C:56]=1[F:65].C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[NH:1]([C:30]([O:32][CH2:33][CH:34]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:40]2[C:35]1=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:31])[C@H:2]([C:27]([O:29][C:60]1[C:55]([F:54])=[C:56]([F:65])[C:57]([F:64])=[C:58]([F:63])[C:59]=1[F:62])=[O:28])[CH2:3][CH2:4][C:5](=[O:26])[NH:6][C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
Reactant: O=C(CC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O)NC(c1ccccc1)(c1ccccc1)c1ccccc1
Reactant: Oc1c(F)c(F)c(F)c(F)c1F
Agent: C(=NC1CCCCC1)=NC1CCCCC1
Solvent: CCOC(C)=O
Solvent: CC(C)OC(C)C
Product: O=C(CC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)Oc1c(F)c(F)c(F)c(F)c1F)NC(c1ccccc1)(c1ccccc1)c1ccccc1

Procedure:
1.5 g (2.27 mmol) of Fmoc-Gln(Trt)-OH×0.5 diisopropyl ether and 0.46 g (2.5 mmol) of pentafluoro-phenol are dissolved in 35 ml of ethyl acetate, cooled to 0° and, while stirring, 0.52 g (2.5 mmol) of dicyclohexylcarbodiimide is added. The mixture is stirred at 0° for 1 hour and at room temperature for 3 hours, and insoluble material is filtered off and washed with tetrahydrofuran. The filtrate is evaporated to dryness, and the residue is dissolved in 30 ml of tetrahydrofuran. Slow addition of petroleum ether while stirring results in crystallization of Fmoc-Gln(Trt)-OPfp; m.p. 185°-187°, [α]D20 =-16.4° (THF).
Reaction SMILES: [CH:1]1([Mg]Br)C[CH2:5][CH2:4][CH2:3][CH2:2]1.C[N:10]1CCCC1.[Cl:15][C:16]1[CH:25]=[C:24](Cl)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1.O>C(OCC)C.C1COCC1.[Cl-].[Zn+2].[Cl-].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[Cl:15][C:16]1[N:10]=[C:24]([CH:25]2[CH2:5][CH2:4][CH2:3][CH2:2][CH2:1]2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1
Reactant: CN1CCCC1
Reactant: Br[Mg]C1CCCCC1
Reactant: Clc1cc(Cl)c2ccccc2n1
Agent: CC(C)(C)[P]([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C(C)(C)C)C(C)(C)C
Agent: [Cl-]
Agent: [Zn+2]
Solvent: O
Solvent: CCOCC
Solvent: C1CCOC1
Product: Clc1nc(C2CCCCC2)c2ccccc2n1
Temperature: 25 °C
Reaction time: 0.33 h

Procedure:
To a solution of 2 M cyclohexylmagnesium bromide in diethyl ether (3.3 mL) was added a solution of 0.5 M zinc chloride in THF (14 mL) under nitrogen atmosphere, and the mixture was stirred at room temperature for 20 min. N-methylpyrrolidine (10 mL) was added, the mixture was stirred for 5 min, followed by addition of Pd(PtBu3)2 (0.13 g) and 2,4-dichloroquinoline (1.0 g), and the mixture was stirred at room temperature for 4 h. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was dried with anhydrous sodium sulfate, the desiccant was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=6:1) to obtain 2-chloro-4-cyclohexylquinazoline (1.1 g).
Reaction SMILES: [NH:1]1[CH2:11][CH2:10][CH2:9][CH:3](C(OCC)=O)[CH2:2]1.[N+:12]([C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=O)([O-:14])=[O:13].[NH2:23][C:24]1[CH:28]=[CH:27][NH:26][N:25]=1>>[C:2]([C:3]1[CH:17]([C:16]2[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=2[N+:12]([O-:14])=[O:13])[C:28]2[C:24](=[N:25][NH:26][CH:27]=2)[NH:23][C:9]=1[CH:9]1[CH2:3][CH2:2][NH:1][CH2:11][CH2:10]1)#[N:1]
Reactant: CCOC(=O)C1CCCNC1
Reactant: Nc1cc[nH]n1
Reactant: O=Cc1ccccc1[N+](=O)[O-]
Product: N#CC1=C(C2CCNCC2)Nc2n[nH]cc2C1c1ccccc1[N+](=O)[O-]

Procedure:
The title compound was prepared from ethyl nipecotate, 2-nitrobenzaldehyde and 3-aminopyrazole in the same manner as in Examples 1001 and 1002.
Reaction SMILES: C([Mg]Cl)(C)(C)C.[F:7][C:8]1[C:13]([C:14]2[C:19]([F:20])=[C:18]([F:21])[C:17]([CH2:22][S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])=[C:16]([F:30])[C:15]=2[F:31])=[C:12]([F:32])[C:11]([F:33])=[C:10]([F:34])[C:9]=1[F:35].[F:36][C:37]([F:48])([F:47])[S:38]([O:40]S(C(F)(F)F)=O)=[O:39].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.O.Cl>O.C(OCC)C>[F:32][C:12]1[C:13]([C:14]2[C:15]([F:31])=[C:16]([F:30])[C:17]([CH:22]([S:38]([C:37]([F:48])([F:47])[F:36])(=[O:40])=[O:39])[S:23]([C:26]([F:27])([F:28])[F:29])(=[O:25])=[O:24])=[C:18]([F:21])[C:19]=2[F:20])=[C:8]([F:7])[C:9]([F:35])=[C:10]([F:34])[C:11]=1[F:33]
Reactant: O=S(=O)(Cc1c(F)c(F)c(-c2c(F)c(F)c(F)c(F)c2F)c(F)c1F)C(F)(F)F
Reactant: O=S(OS(=O)C(F)(F)F)C(F)(F)F
Agent: CC(C)(C)[Mg]Cl
Agent: Cl
Agent: O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F
Solvent: CCOCC
Solvent: O
Product: O=S(=O)(C(c1c(F)c(F)c(-c2c(F)c(F)c(F)c(F)c2F)c(F)c1F)S(=O)(=O)C(F)(F)F)C(F)(F)F
Temperature: -78 °C
Reaction time: 0.5 h
Yield: 94 %

Procedure:
A tert-butyl magnesium chloride (5 mL, 10 mmol, 2.0 M diethylether solution) was added to a diethylether (120 mL) solution dissolved with {4-(pentafluorophenyl)-2,3,5,6-tetrafluorophenyl}(triflyl)methane (4.6 g, 10 mmol), at −78° C. under argon atmosphere. After the reaction solution was stirred for 0.5 hour at −78° C., it was further stirred for 0.5 hour at 0° C. Then, the solution was cooled again to −78° C., trifluoromethane sulfinic acid anhydride (0.84 mL, 5 mmol) was added, and the resultant solution was stirred for 2 hours at room temperature. Further, tert-butyl magnesium chloride (3.75 mL, 7.5 mmol, 2.0 M diethylether solution) was added at −78° C. After the reaction solution was stirred at −78° C. for 0.5 hour, it was stirred at 0° C. for 0.5 hour. The solution was cooled again to −78° C., trifluoromethanesulfonic acid anhydride (0.84 mL, 5 mmol) was added, and the resultant solution was stirred for 2 hours at room temperature. After the reaction was completed, water was added, further neutralized with 1 M hydrochloric acid water, and the water phase was washed with hexane. Then, said water phase was acidified with 4 M hydrochloric acid water, and extracted with diethylether. The organic phase was dried with magnesium sulfate, filtrated, and the solvent was removed under reduced pressure. The crude product was sublimated (8 to 9 Pa, 150° C., and the aimed {4-(pentafluorophenyl)-2,3,5,6-tetrafluorophenyl}bis(triflyl)methane (2.79 g, 4.7 mmol, 47% yield) was isolated. 1H NMR (CDCl3, 300 MHz) δ 6.32 (s, 1H, CH), 19F NMR (CDCl3, 282 MHz) δ−75.1 (s, 6F, 2CF3), −127.72 to −127.58 (m, 1F), −133.43 (dt, J=10.2, 21.3 Hz, 1F), −134.60 (dt, J=9.4, 21.3 Hz, 1F), −137.08 to −137.35 (m, 2F), −140.07 (br, 1F), −148.38 (t, J=21.3 Hz, 1F), −160.01 (dt, J=6.2, 21.3 Hz, 2F).
Reaction SMILES: [Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]I)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li]C(C)(C)C.[CH3:24][O:25][C:26]1[CH:35]=[C:34]2[C:29]([C:30](=[O:43])[C:31]([CH3:42])([C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)[CH2:32][O:33]2)=[CH:28][CH:27]=1.[NH4+].[Cl-]>CCCCC.C(OCC)C.C1COCC1>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:30]1([OH:43])[C:29]2[C:34](=[CH:35][C:26]([O:25][CH3:24])=[CH:27][CH:28]=2)[O:33][CH2:32][C:31]1([CH3:42])[C:36]1[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
Reactant: CC(C)(C)[Si](C)(C)OCCCCCCCCCI
Reactant: COc1ccc2c(c1)OCC(C)(c1cccnc1)C2=O
Agent: [Cl-]
Agent: [Li]C(C)(C)C
Agent: [NH4+]
Solvent: CCOCC
Solvent: CCCCC
Solvent: C1CCOC1
Product: COc1ccc2c(c1)OCC(C)(c1cccnc1)C2(O)CCCCCCCCCO[Si](C)(C)C(C)(C)C
Temperature: -78 °C
Reaction time: 0.17 h
Yield: 75.1 %

Procedure:
To a solution of 9-(t-butyldimethylsilyloxy)nonyl iodide (1.05 g, 2.7 mmol) in pentane (10 ml) and diethylether (7 ml) was added at −78° C. t-BuLi (1.64M in pentane, 3.62 ml, 5.94 mmol), which was stirred for 10 minutes and then stirred for 1 h at room temperature. The mixture was cooled to −78° C. again, and a solution of 7-methoxy-3-methyl-3-(3-pyridyl)chroman-4-one (436 mg, 1.62 mmol) dissolved in THF (5 ml) was added thereto. The resulting solution was stirred at −78° C. for 30 minutes, and then stirred for 1 h at room temperature. The reaction solution was neutralized under ice-cooling using saturated aqueous NH4Cl solution, extracted with AcOEt, and washed with brine. The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. The recidue was purified by chromatography on silica-gel with 70% AcOEt/hexane to give 642 mg (75%) of 4-[9-(t-butyldimethylsilyloxy)nonyl]-4-hydroxy-7-methoxy-3-methyl-3-(3-pyridyl)chroman.
Reaction SMILES: [C:1](Cl)(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH2:17]([O:19][C:20](=[O:39])[CH2:21][N:22]([C:29](=[O:38])[C:30]1[CH:35]=[C:34]([NH2:36])[CH:33]=[C:32]([NH2:37])[CH:31]=1)[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:18].C(N([CH2:45][CH3:46])CC)C>C1COCC1>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][N:22]([CH2:21][C:20]([O:19][CH2:17][CH3:18])=[O:39])[C:29](=[O:38])[C:30]1[CH:35]=[C:34]([NH:36][C:1](=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:33]=[C:32]([NH:37][C:1](=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:45][CH3:46])[CH:31]=1)[CH3:28]
Reactant: CCOC(=O)CN(CC(=O)OCC)C(=O)c1cc(N)cc(N)c1
Reactant: CCCCCCCCCCCCCC(=O)Cl
Reactant: CCN(CC)CC
Solvent: C1CCOC1
Product: CCCCCCCCCCCCCC(=O)Nc1cc(NC(=O)CCCCCCCCCCCCC)cc(C(=O)N(CC(=O)OCC)CC(=O)OCC)c1
Reaction time: 0.5 h
Yield: 91.3 %

Procedure:
A solution of 1.9 ml (7 mmol) of myristoyl chloride in 10 ml of anhydrous THF was added dropwise to a stirred, ice cooled mixture of 1.0 g (3.09 mmol) of N-(3,5-diaminobenzoyl)-N-(2-ethoxy-2-oxoethyl)glycine ethyl ester and 1.7 ml (12.4 mmol) of triethylamine in 20 ml of anhydrous THF. The reaction mixture was stirred in the cooling bath for 30 minutes and then at room temperature for 24 hours. The solvent was removed at reduced pressure and the residue was extracted with ethyl acetate. After washing with NaHCO3 solution, the dried extract was concentrated to an oil which was purified by chromatography on 120 g of silica gel using 40% ethyl acetate-hexane to give 2.1 g (91% yield) of N-(2-ethoxy-2-oxoethyl)-N-[3,5-bis(1-oxotetradecylamino)benzoyl]glycine ethyl ester as a yellow oil. The nmr and mass spectra were consistent with the structure.
Reaction SMILES: [F:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.C(#N)C.C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(OCC)(=O)C.O>[CH2:23]([O:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([O:12][CH3:13])[CH:3]=[C:2]([F:1])[CH:7]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
Reactant: BrCc1ccccc1
Reactant: COc1cc(F)cc(O)c1[N+](=O)[O-]
Agent: O=C([O-])[O-]
Agent: [K+]
Solvent: CCOC(C)=O
Solvent: O
Solvent: CC#N
Product: COc1cc(F)cc(OCc2ccccc2)c1[N+](=O)[O-]
Yield: 98.8 %

Procedure:
A mixture of 5-fluoro-3-methoxy-2-nitrophenol(0.56 g), acetonitrile(5 mL), potassium carbonate(0.46 g) and benzyl bromide(0.56 g) was stirred at reflux for 2 h. The cooled mixture was treated with water and ethyl acetate and the organic phase was separated, washed with brine, dried and evaporated to dryness. The residue was purified by flash chromatography eluting with increasingly polar mixtures of ethyl acetate and hexane to give the product (0.82 g), (m/e278, MH+).
Reaction SMILES: [N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[CH:12]([NH:15][C:16](=[O:21])[CH2:17][C:18]([CH3:20])=[O:19])([CH3:14])[CH3:13].N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1>[CH:12]([NH:15][C:16](=[O:21])[CH2:17][C:18]([CH:20]=[CH:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])=[O:19])([CH3:14])[CH3:13]
Reactant: O=Cc1ccccc1[N+](=O)[O-]
Reactant: CC(=O)CC(=O)NC(C)C
Solvent: C1CCNCC1
Solvent: CC(=O)O
Solvent: c1ccccc1
Product: CC(C)NC(=O)CC(=O)C=Cc1ccccc1[N+](=O)[O-]
Yield: 78.3 %

Procedure:
o-Nitrobenzaldehyde (43.4 g, 0.29 mole) and acetoacetic isopropylamide (40.0 g, 0.29 mole) are dissolved in benzene (150 ml) and thereto are added piperidine (1.15 ml) and acetic acid (3.45 ml), and the mixture is refluxed and the produced water is removed. After the stoichiometic amount of water is distilled off, the reaction is stopped. After the reaction, the solvent is distilled off under reduced pressure, and the residue is recrystallized from ethanol to give the title compound (62.7 g, yield 78.4%) as colorless prisms, m.p. 132°-135° C.
Reaction SMILES: CCCNCC(O)CO[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=1[C:15]([CH2:17]CC1C=CC=CC=1)=[O:16].Cl.[OH:27]C(CNCCC)CO[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37](=[O:46])CCC1C=CC=CC=1.[Na].ClCC1OC1.C(N)CC.Cl>>[OH:27][CH2:17][C:15]([C:14]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:16].[CH:37](=[O:46])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:31]=1
Reactant: CCCNCC(O)COc1ccccc1C(=O)CCc1ccccc1
Agent: Cl
Agent: [Na]
Solvent: ClCC1CO1
Solvent: CCCN
Product: O=C(CO)c1ccccc1
Product: O=Cc1ccccc1

Procedure:
Propafenone (2'-(2-hydroxy-3-propylaminopropoxy)-3-phenylpropiophenone hydrochloride, German Pat. No. 2,001,431) is a substance having an anti-arrhythmic action. According to the said German patent, it is obtained by reacting 2-hydroxy-omega-phenylpropiophenone (as the sodium salt) with 1-chloro-2,3-epoxypropane and then reacting the resulting 2-(2',3'-epoxypropyl)-omega-phenylpropiophenone with n-propylamine and converting the product to the hydrochloride. This process gives a yield of only about 66%. Moreover, the starting material (2-hydroxy-omega-phenylpropiophenone) required for the reaction can only be obtained with difficulty from 2-hydroxyacetophenone by condensing with benzaldehyde and then hydrogenating the reaction product.