Reaktion #684252

Reaktionsgleichung

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

Lösungsmittel

n-butylalcohol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis refluxed for 7.5 hours with a slow stream of nitrogen bubbling through the mixture
2. 2
   EinengenThe mixture is then concentrated in vacuo
3. 3
   Extraktionextracted with methylene chloride
4. 4
   SonstigeThe extract was dried
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue is chromatographed on silica gel (400 g.) with 2% methanol- 98% CHCl3
7. 7
   WaschenThe product eluted from the column
8. 8
   Sonstigeis crystallized from ethyl acetate-Skellysolve B hexanes
9. 9
   Sonstigeto give 2.62 g

Vorschrift

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.

Quelle