Ethyl formate → HCID 12234603, compound

HRID 442327Notes

Reaction equation

HRID 442327 reaction equation
[CH:1](OCC)=[O:2].[CH3:6][N:7]1[C:13]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:12]=2[CH:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[NH:10][CH2:9][C:8]1=[O:25]>ClC1C=CC=CC=1>[CH3:6][N:7]1[C:13]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:12]=2[CH:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:10]([CH:1]=[O:2])[CH2:9][C:8]1=[O:25]

Participants

4

Reactant 2

HCID 8025Ethyl formateHCID 30819844,5-Dihydrodiazepam

Product 1

HCID 12234603HCID 12234603, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

6 ml. of ethyl formate are added to a solution of 1.4 g. (5 mmoles) of 1-methyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one in 5 ml. of chlorobenzene, and the reaction mixture is maintained at the boiling point of the solvent for 3 hours. Thereafter the solvent is evaporated under reduced pressure, and the oily residue is solidified by treating it with 20 ml. of dry ether. 108 g. (68.6 %) of 1-methyl-4-formyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one are obtained; m.p.: 167°-169° C. The melting point does not change after recrystallization from ethanol. Rf2 = 0.5.

Workup

  1. customThereafter the solvent is evaporated under reduced pressure
  2. additionby treating it with 20 ml

Sources & evidence

ORD record
ord-3bd60f24588546f3a89469a081b6a3da
Source dataset
uspto-grants-1977_08
Patent number
US04045433

Reaction notes

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