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

HRID 5942

반응식

HRID 5942 반응식
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]

참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran3회HCID 11167Methyl isothiocyanateHCID 197946762-[4-(1-Imidazolyl)-phenyl]propionitrileHCID 23665647Potassium tert-butoxide

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-274c947a2e0049788e83af50650c54b2
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246958

연결된 노트

불러오는 중…