Реакция #684252

Уравнение реакции

1,3-dihydro-7-chloro-5-phenyl-2H-1,4-benzodiazepine-2-thione

cyanoacetic acid hydrazide

→

8-Chloro-6-phenyl-4H-s-triazolo[4,3-a][1,4]-benzodiazepine-1-acetonitrile

Растворители

n-butylalcohol

Условия реакции

Обработка

1. 1
   Температураis refluxed for 7.5 hours with a slow stream of nitrogen bubbling through the mixture
2. 2
   КонцентрированиеThe mixture is then concentrated in vacuo
3. 3
   Экстракцияextracted with methylene chloride
4. 4
   ДругоеThe extract was dried
5. 5
   Концентрированиеconcentrated
6. 6
   ДругоеThe residue is chromatographed on silica gel (400 g.) with 2% methanol- 98% CHCl3
7. 7
   ПромывкаThe product eluted from the column
8. 8
   Другоеis crystallized from ethyl acetate-Skellysolve B hexanes
9. 9
   Другоеto give 2.62 g

Методика

A mixture of 1,3-dihydro-7-chloro-5-phenyl-2H-1,4-benzodiazepine-2-thione (5.72 g., 0.02 mole), cyanoacetic acid hydrazide (5.95 g., 0.06 mole) and n-butylalcohol (275 ml.) is refluxed for 7.5 hours with a slow stream of nitrogen bubbling through the mixture. The mixture is then concentrated in vacuo. The resulting residue is suspended in water and extracted with methylene chloride. The extract was dried and concentrated. The residue is chromatographed on silica gel (400 g.) with 2% methanol- 98% CHCl3. The product eluted from the column is crystallized from ethyl acetate-Skellysolve B hexanes to give 2.62 g. of 8-chloro-6-phenyl-4H-s-triazolo[4,3a][1,4]benzodiazepine-1-acetonitrile of melting point 198°-201° C.

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