Tetrahydrofuran → N-methyl-2-[4-(1-imidazolyl)-phenyl]-2cyanothiopropionamide

HRID 5942

Reaction equation

HRID 5942 reaction equation
O1CCCC1.[N:6]1([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:20])[C:18]#[N:19])=[CH:13][CH:12]=2)[CH:10]=[CH:9][N:8]=[CH:7]1.CC(C)([O-])C.[K+].[CH3:27][N:28]=[C:29]=[S:30]>O>[CH3:27][NH:28][C:29](=[S:30])[C:17]([C:14]1[CH:13]=[CH:12][C:11]([N:6]2[CH:10]=[CH:9][N:8]=[CH:7]2)=[CH:16][CH:15]=1)([C:18]#[N:19])[CH3:20]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 11167Methyl isothiocyanateHCID 197946762-[4-(1-Imidazolyl)-phenyl]propionitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 9795435N-methyl-2-[4-(1-imidazolyl)-phenyl]-2cyanothiopropionamideYield 54.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 10 ml tetrahydrofuran solution containing 1.00 g (5.1 mmole) of 2-[4-(1-imidazolyl)-phenyl]propionitrile was added a 10 ml tetrahydrofuran solution containing 0.69 g (6.2 mmole) of potassium tert-butoxide at 0 C. After stirring for 0.5 hour, a 5 ml tetrahydrofuran solution containing 0.45 g (6.2 mmole) of methyl isothiocyanate was added to the mixture and the mixture was stirred at room temperature for 2 hours. Water was added to the mixture and the mixture was extracted with 20 ml of ethyl acetate, dried and condensed under reduced pressure, and then purified by silica gel chromatography and condensed. The resulting condensate was suspended in 30 ml of toluene and the suspension was refluxed under heating for 0.5 hour and a solid was collected by filtration to obtain 0.75 g (yield: 54 %) of N-methyl-2-[4-(1-imidazolyl)-phenyl]-2cyanothiopropionamide as a crystalline solid.

Workup

  1. additionwas added to the mixture
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. extractionthe mixture was extracted with 20 ml of ethyl acetate
  4. customdried
  5. customcondensed under reduced pressure
  6. custompurified by silica gel chromatography and condensed
  7. temperaturethe suspension was refluxed
  8. temperatureunder heating for 0.5 hour
  9. filtrationa solid was collected by filtration

Sources & evidence

ORD record
ord-274c947a2e0049788e83af50650c54b2
Source dataset
uspto-grants-1993_09
Patent number
US05246958

Linked notes

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