Tetrahydrofuran → N-methyl-2-(4-chlorophenyl)-2-cyano-5-phenylthiovaleroamide

HRID 5939

Reaction equation

HRID 5939 reaction equation
O1CCCC1.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14]#[N:15])=[CH:9][CH:8]=1.CC(C)([O-])C.[K+].[CH3:31][N:32]=[C:33]=[S:34]>O>[CH3:31][NH:32][C:33](=[S:34])[C:13]([C:10]1[CH:11]=[CH:12][C:7]([Cl:6])=[CH:8][CH:9]=1)([C:14]#[N:15])[CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 11167Methyl isothiocyanateHCID 141477222-(4-Chlorophenyl)-5-phenylvaleronitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 19794677N-methyl-2-(4-chlorophenyl)-2-cyano-5-phenylthiovaleroamideYield 52.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a tetrahydrofuran solution containing 1.78 g (6.6 mmole) of 2-(4-chlorophenyl)-5-phenylvaleronitrile was added a tetrahydrofuran solution containing 0.77 g (6.9 mmole) of potassium tert-butoxide at 0° C. After stirring for 30 minutes, a tetrahydrofuran solution containing 0.5 g (6.8 mmol) of methyl isothiocyanate was added to the mixture and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, dried and condensed under reduced pressure, and then purified by silica gel chromatography to obtain 1.19 g (yield: 52.4 %) of N-methyl-2-(4-chlorophenyl)-2-cyano-5-phenylthiovaleroamide as a crystal.

Workup

  1. additionwas added to the mixture
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. customdried
  5. customcondensed under reduced pressure
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-9eff2be66d41411fafc7473e558a11ff
Source dataset
uspto-grants-1993_09
Patent number
US05246958

Linked notes

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