反応 #64343

反応方程式

potassium t-butoxide

6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-one

phenyl isothio-cyanate

N,N-dimethylformamide

→

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

収率 47.9%

溶媒

acetic acid

反応条件

後処理

1. 1
   温度cooling
2. 2
   温度cooling
3. 3
   抽出extracted with diethyl ether
4. 4
   洗浄The extract was washed with water
5. 5
   乾燥dried over sodium sulfate
6. 6
   その他the ether layer was removed by distillation
7. 7
   その他The residue was purified by silica gel column chromatography (developing solution: CH2Cl2)

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.

出典