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

HRID 36065

反応式

HRID 36065 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5b12e05a7622475082ec0de4fcdad81a
出典データセット
uspto-grants-1995_05
特許番号
US05412117

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