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

HRID 36066

Reaction equation

HRID 36066 reaction equation
[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

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 7672Phenyl isocyanateHCID 148695546-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-oneHCID 23665647Potassium tert-butoxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-66ed7a06d95b4269b26ca4cfa7ade68e
Source dataset
uspto-grants-1995_05
Patent number
US05412117

Linked notes

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