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

HRID 36066

반응식

HRID 36066 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].CC(C)([O-])C.[K+].CN(C)C=O.[C:27]1([N:33]=[C:34]=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(O)(=O)C>[C:27]1([NH:33][C:34]([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])=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

6

반응물 4

HCID 6228Dimethylformamide2회HCID 7672Phenyl isocyanateHCID 148695546-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-oneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 54719680N-phenyl-6-cyano-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-carboxamide수율 21.4%

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, 0.39 g of potassium t-butoxide, and 5 ml of dried N,N-dimethylformamide was added dropwise a mixture of 0.42 g of phenyl isocyanate and 1.5 ml of dried N,N-dimethylformamide while stirring under cooling with ice. After stirring for 4 hours under ice-cooling, ice-water was added thereto, and the mixture was made acidic with acetic acid and extracted with diethyl ether. The ether layer was washed with water and dried over sodium sulfate. Diethyl ether was removed by distillation, and the residue was purified by silica gel column chromatography (developing solution: CH2Cl2) to obtain 0.17 g of N-phenyl-6-cyano-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-carboxamide represented by formula shown below.

후처리

  1. additionwas added dropwise
  2. temperatureunder cooling with ice
  3. stirringAfter stirring for 4 hours under ice-
  4. temperaturecooling
  5. extractionextracted with diethyl ether
  6. washThe ether layer was washed with water
  7. dry with materialdried over sodium sulfate
  8. customDiethyl ether was removed by distillation
  9. customthe residue was purified by silica gel column chromatography (developing solution: CH2Cl2)

출처 및 근거

ORD 기록
ord-66ed7a06d95b4269b26ca4cfa7ade68e
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05412117

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