Methyl Isocyanate → HCID 20486169, compound

HRID 1995888Notes

Reaction equation

HRID 1995888 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[NH:13][C:12](=[O:14])[CH2:11][NH:10][CH:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]=2[CH:21]=1)([O-:3])=[O:2].[CH3:22][N:23]=[C:24]=[O:25]>CCOCC>[CH3:22][NH:23][C:24]([N:10]1[CH:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8]2[CH:21]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[NH:13][C:12](=[O:14])[CH2:11]1)=[O:25]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 20486171HCID 20486171, compound

Product 1

HCID 20486169HCID 20486169, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5.6 g. (0.2 moles) of 7-nitro-5-phenyl-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one are suspended in 25 ml. of dry ether, and 4.8 ml. (0.08 moles) of methyl isocyanate are added to the suspension. The reaction mixture is stirred at room temperature for 16 hours, thereafter the solid crystalline substance is filtered off and washed with ether. 6.03 g. (96.7%) of 4-methylcarbamoyl-5-phenyl-7-nitro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one are obtained, m.p.: 176°-180° C. After recrystallization from ethanol, the product melts at 179°-180° C. Rf2 =0.4.

Workup

  1. filtrationthe solid crystalline substance is filtered off
  2. washwashed with ether

Sources & evidence

ORD record
ord-645a77381d2645729cae7a6e4f4c96c6
Source dataset
uspto-grants-1983_09
Patent number
US04406835

Reaction notes

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