反応 #64352

反応方程式

N-methyl-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide

p-toluenesulfonyl chloride

triethylamine

acetonitrile

→

titled compound

N-Cyano-N'-methyl-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carboxamidine

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度at reflux for 30 minutes
3. 3
   その他The solvent was removed by distillation
4. 4
   workup.ADDITIONto the residue were added 0.27 g of cyanamide, 0.17 g of sodium hydride, and 4 ml of ethanol
5. 5
   温度by heating
6. 6
   温度under reflux for 30 minutes
7. 7
   workup.ADDITIONConcentrated hydrochloric acid and water were added to the reaction mixture
8. 8
   抽出the mixture was extracted with methylene chloride
9. 9
   洗浄The organic layer was washed successively with a 2N potassium carbonate aqueous solution
10. 10
    乾燥a saturated sodium chloride aqueous solution and dried over magnesium sulfate
11. 11
    その他The solvent was removed by distillation
12. 12
    その他recrystallized from a mixture of ethyl acetate and diethyl ether

実験手順

A mixture of 0.56 g of N-methyl-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide, 0.39 g of p-toluenesulfonyl chloride, 0.21 g of triethylamine, and 3 ml of acetonitrile was heated at reflux for 30 minutes. The solvent was removed by distillation, and to the residue were added 0.27 g of cyanamide, 0.17 g of sodium hydride, and 4 ml of ethanol, followed by heating under reflux for 30 minutes. Concentrated hydrochloric acid and water were added to the reaction mixture, and the mixture was extracted with methylene chloride. The organic layer was washed successively with a 2N potassium carbonate aqueous solution and a saturated sodium chloride aqueous solution and dried over magnesium sulfate. The solvent was removed by distillation, and the residue was subjected to silica gel column chromatography (developing solution: n-hexane:ethyl acetate=1:1) and then recrystallized from a mixture of ethyl acetate and diethyl ether to obtain 50 mg of the titled compound.

出典