Ammonia → Uxepam

HRID 66557Notes

Reaction equation

HRID 66557 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:7]=2[CH:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:5]([C:20](Cl)=[O:21])[CH2:4][C:3]1=[O:23].[NH3:24]>CO>[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:7]=2[CH:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:5]([C:20](=[O:21])[NH2:24])[CH2:4][C:3]1=[O:23]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 20486168HCID 20486168, compound

Product 1

HCID 68787UxepamYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 1.7 g. (4.87 mmoles) of 1-methyl-4-chlorocarbonyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one in 3.5 ml. of concentrated ammonia and 7 ml. of methanol is stirred at room temperature overnight. The mixture is diluted with 30 ml. of water, the separated crude product is filtered off, and recrystallized from ethanol without drying. 1.16 g. (72%) of 1-methyl-4-carbamoyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one are obtained; m.p.: 212°-215° C.

Workup

  1. additionA suspension of 1.7 g
  2. additionThe mixture is diluted with 30 ml
  3. customof water, the separated crude product
  4. filtrationis filtered off
  5. customrecrystallized from ethanol
  6. customwithout drying

Sources & evidence

ORD record
ord-40bef482622245f78ab47a155d0a1cd7
Source dataset
uspto-grants-1982_08
Patent number
US04342755

Reaction notes

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