Hydrochloric Acid → HCID 15587237, compound

HRID 2059126Notes

Reaction equation

[CH2:1]([CH:3]([C:7]1[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[CH:18][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])=O)[C:4]([CH3:6])=O)[CH3:2].Cl.O.[NH2:28][NH2:29].[OH-].[Na+]>O.CO.C(O)(=O)C>[Cl:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:9]1[C:8]2[CH:18]=[C:19]([O:24][CH3:25])[C:20]([O:22][CH3:23])=[CH:21][C:7]=2[CH:3]([CH2:1][CH3:2])[C:4]([CH3:6])=[N:29][N:28]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 10.37 g (28.9 mmoles) of 2-(1-ethylacetonyl)-4,5-dimethoxy-2'-chlorobenzophenone, 10.5 ml of glacial acetic acid and 2.65 ml of concentrated hydrochloric acid is heated to 95° C. under stirring. The mixture is cooled to 60° C., and 2.14 ml of 98% hydrazine hydrate are added to the mixture in portions, whereupon the temperature of the mixture raises to 85° C. After 30 minutes a solution of 1.44 g of sodium hydroxide in 4.5 ml of water is added to the mixture, followed by 10 ml of methanol. The resulting solution is poured into 130 ml of water, and the separated 5H-2,3-benzodiazepine derivative is isolated. 9.04 g (88%) of the title compound are obtained; m.p.: 129°-131° C. C20H21ClN2O2 =356.9. The crude product can be recrystallized e.g. from ethanol. The product with the highest purity grade melts at 147°-149° C. The rhodanide salt of the title compound ([C20H22ClN2O2 ]SCN=425.95) melts at 169°-171° C. after recrystallization from isopropanol.

Workup

temperatureThe mixture is cooled to 60° C.
temperatureraises to 85° C

Sources & evidence

ORD record: ord-2c60d4efde064c8587f3b70fcb7f8726
Source dataset: uspto-grants-1982_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04322346

Reaction notes

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