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

HRID 36065

반응식

HRID 36065 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].[C:16]1([N:22]=[C:23]=[S:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CN(C)C=O.CC(C)([O-])C.[K+]>C(O)(=O)C>[C:16]1([NH:22][C:23]([C:8]2[C:7]3[CH:15]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=3[O:11][C:10]([CH3:13])([CH3:12])[C:9]=2[OH:14])=[S:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 7673Phenyl IsothiocyanateHCID 148695546-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-oneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 135720099N-phenyl-6-cyano-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide수율 47.9%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a mixture of 0.5 g of 6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-one, 0.37 g of phenyl isothio-cyanate, and 5 ml of dried N,N-dimethylformamide was added 0.31 g of potassium t-butoxide with under ice-cooling, followed by stirring for 5 hours under ice-cooling. Ice-water was added thereto, and the mixture was made acidic with acetic acid and extracted with diethyl ether. The extract was washed with water and dried over sodium sulfate, and the ether layer was removed by distillation. The residue was purified by silica gel column chromatography (developing solution: CH2Cl2) to obtain 0.4 g of N-phenyl-6- cyano-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide represented by formula shown below.

후처리

  1. temperaturecooling
  2. temperaturecooling
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with water
  5. dry with materialdried over sodium sulfate
  6. customthe ether layer was removed by distillation
  7. customThe residue was purified by silica gel column chromatography (developing solution: CH2Cl2)

출처 및 근거

ORD 기록
ord-5b12e05a7622475082ec0de4fcdad81a
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05412117

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