Semicarbazide → Aminobenzophenone semicarbazone

HRID 614196

Reaction equation

[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[NH2:16][NH:17][C:18]([NH2:20])=[O:19]>>[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4](=[N:16][NH:17][C:18]([NH2:20])=[O:19])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

Reactant 2

HCID 5196Semicarbazide

HCID 760802-Aminobenzophenone2×

Product 1

HCID 620280Aminobenzophenone semicarbazone

Procedure

A number of methods for preparing 1,3,4-benzotriazepine-2-ones have been described in the literature. In general, the compounds are prepared by either of two methods from a 2-aminobenzophenone. In the first method, the 2-aminobenzophenone is treated with semicarbazide to give an aminobenzophenone semicarbazone. This product is cyclized to give the benzotriazepine-2-one. See Bull. Chem. Soc. Jap., 43, 135-138 (1970); Japanese publications 70 11,148 (CA 73:25544a) and 70 11,147 (CA 73:25545b). Alternately, a 2-amino-benzophenone hydrazone is treated with phosgene to give the desired benzotriazepine-2-one. See U.S. Pat. No. 3,176,008; J. Pharm. Sci. 63 (b), 838-41 (1974) and J. Med. Chem. 7(3), 386 (1964).

Sources & evidence

ORD record: ord-effc535b2291428fb6cc2d67d24afefc
Source dataset: uspto-grants-1979_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04144233

Linked notes

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