Dimethylformamide → N-methyl-6-cyano-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide

HRID 36062

반응식

HRID 36062 반응식
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C:9](=[O:14])[CH2:8][C:7]=2[CH:15]=1)#[N:2].[CH3:16][N:17]=[C:18]=[S:19].CN(C)C=O.CC(C)([O-])C.[K+]>C(O)(=O)C>[CH3:16][NH:17][C:18]([C:8]1[C:7]2[CH:15]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=2[O:11][C:10]([CH3:13])([CH3:12])[C:9]=1[OH:14])=[S:19]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11167Methyl isothiocyanateHCID 148695546-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-oneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 135720096N-methyl-6-cyano-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide수율 68.5%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a mixture of 1.5 g of 6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-one, 0.6 g of methyl isothio-cyanate, and 15 ml of dried N,N-dimethylformamide was added 0.93 g of potassium t-butoxide with stirring under ice-cooling, followed by stirring for 4 hours under ice-cooling. Ice-water was added to the reaction mixture, and the mixture was made acidic with acetic acid and then extracted with diethyl ether. The ether layer was washed with water and dried over sodium sulfate. The ether layer was removed by distillation, and the residue was recrystallized from ethanol to yield 1.4 g of N-methyl-6-cyano-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide represented by formula shown below.

후처리

  1. temperaturecooling
  2. stirringby stirring for 4 hours under ice-
  3. temperaturecooling
  4. extractionextracted with diethyl ether
  5. washThe ether layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. customThe ether layer was removed by distillation
  8. customthe residue was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-de48dd21366944da9ff0804dea9a9368
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05412117

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