Methyl isothiocyanate → N-methyl-2-(4-chlorophenyl)-2-cyano-thiopropionamide

HRID 5940

반응식

HRID 5940 반응식
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH:6]([C:14]#[N:15])[CH2:7]C2C=CC=CC=2)=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[Li+].[CH3:26][N:27]=[C:28]=[S:29]>O1CCCC1>[CH3:26][NH:27][C:28](=[S:29])[C:6]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:17][CH:16]=1)([C:14]#[N:15])[CH3:7]

참가 물질

5

반응물 3

HCID 11167Methyl isothiocyanateHCID 2235642-(4-Chlorophenyl)-3-phenylpropanenitrileHCID 2724682Lithium diisopropylamide

생성물 1

HCID 19794675N-methyl-2-(4-chlorophenyl)-2-cyano-thiopropionamide수율 31.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a 10 ml tetrahydrofuran solution containing 1.00 g (6 mmole) of 4-chlorophenylmethylbenzylcyanide was added a 3.2 ml tetrahydrofuran solution containing 2 M of lithium diisopropylamide at -60° C. After stirring for 30 minutes under the same conditions, a 5 ml tetrahydrofuran solution containing 0.44 g (6 mmol) of methyl isothiocyanate was added to the mixture and the mixture was allowed to stand at room temperature overnight. The solvent was removed from the reaction mixture under reduced pressure and water was added to the residue. The mixture was extracted with 50 ml of ethyl acetate, dried and condensed under reduced pressure, and then purified by silica gel chromatography and recrystallized from hexane to obtain 0.45 g (yield: 31.4 %) of N-methyl-2-(4-chlorophenyl)-2-cyano-thiopropionamide.

후처리

  1. additionwas added to the mixture
  2. waitto stand at room temperature overnight
  3. customThe solvent was removed from the reaction mixture under reduced pressure and water
  4. additionwas added to the residue
  5. extractionThe mixture was extracted with 50 ml of ethyl acetate
  6. customdried
  7. customcondensed under reduced pressure
  8. custompurified by silica gel chromatography
  9. customrecrystallized from hexane

출처 및 근거

ORD 기록
ord-97a71ab8b30846a79c74a25e489cdea9
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246958

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