Chemistry
Triazolam is synthesized according to a method that contains a key stage of benzodiazepine synthesis—the reaction of o-aminobenzophenones with α-amino acid derivatives. In the given example, the reaction of 2-amino-2′,5-dichlorobenzophenone with glycine ethyl ester gives 7-chloro-5-(2-chlorophenyl)-2,3-dihydro-1-H-1,4-benzodiazepin-2-one. By interacting this with phosphorus pentasulfide, the carbonyl group is transformed into a thiocarbonyl group, giving 7-chloro-5-(2-chlorophenyl)-2,3-dihydro-1-H-1,4-benzodiazepin-2-thione. The resulting cyclic thioamide on interaction with acetylhydrazine, gives the corresponding acetylhydrazone, which upon heating cyclizes into triazolam.
- J.B. Hester, Jr., Ger. Pat. 2.012.190 (1970).
- J.B. Hester, Jr., U.S. Pat. 3.701.782 (1972).
- J.B. Hester, Jr., U.S. Pat. 3.987.052 (1976).
- G.A. Archer, L.H. Sternbach, U.S. Pat. 3.422.091 (1969).
- G.A. Archer, L.H. Sternbach, J. Org. Chem., 29, 231 (1964).
- J.B. Hester, A.D. Rudzik, B.V. Kamdar, J. Med. Chem., 14, 1078 (1971).
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