반응 #64352

반응 방정식

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

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도at reflux for 30 minutes
3. 3
   기타The 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
   온도by heating
6. 6
   온도under reflux for 30 minutes
7. 7
   workup.ADDITIONConcentrated hydrochloric acid and water were added to the reaction mixture
8. 8
   추출the mixture was extracted with methylene chloride
9. 9
   세척The organic layer was washed successively with a 2N potassium carbonate aqueous solution
10. 10
    건조a saturated sodium chloride aqueous solution and dried over magnesium sulfate
11. 11
    기타The solvent was removed by distillation
12. 12
    기타recrystallized from a mixture of ethyl acetate and diethyl ether

실험 절차

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.

출처