تفاعل #64352

معادلة التفاعل

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

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated
2. 2
   درجة الحرارةat reflux for 30 minutes
3. 3
   أخرىThe 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
   درجة الحرارةby heating
6. 6
   درجة الحرارةunder reflux for 30 minutes
7. 7
   workup.ADDITIONConcentrated hydrochloric acid and water were added to the reaction mixture
8. 8
   استخلاصthe mixture was extracted with methylene chloride
9. 9
   غسيلThe organic layer was washed successively with a 2N potassium carbonate aqueous solution
10. 10
    تجفيفa saturated sodium chloride aqueous solution and dried over magnesium sulfate
11. 11
    أخرىThe solvent was removed by distillation
12. 12
    أخرىrecrystallized from a mixture of ethyl acetate and diethyl ether

الإجراء التجريبي

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.

المصدر