Ethyl isocyanate → (E)-5-(3,4-dichlorostyryl)-N-ethyl-2,3-dihydro-1H-1,4-benzodiazepine-1-carboxamide

HRID 48350Notes

Reaction equation

HRID 48350 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH:5]=[CH:6][C:7]1=[N:8][CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]1=2.[CH2:22]([N:24]=[C:25]=[O:26])[CH3:23]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH:5]=[CH:6][C:7]1=[N:8][CH2:9][CH2:10][N:11]([C:25]([NH:24][CH2:22][CH3:23])=[O:26])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]1=2

Participants

3

Reactant 2

HCID 8022Ethyl isocyanate2×HCID 69892837HCID 69892837, compound

Product 1

HCID 69892197(E)-5-(3,4-dichlorostyryl)-N-ethyl-2,3-dihydro-1H-1,4-benzodiazepine-1-carboxamideYield 41.2%

Procedure

A solution of 32 mg (0.1 mmol) of (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1H-benzo-1,4-diazepine and 10 mg (0.14 mmol) of ethyl isocyanate was heated at 85° C. for 48 hours, a further 10 mg of ethyl isocyanate being added after 6 hours and again after 30 hours. The solvent was removed by evaporation and the residue chromatographed on silica gel using dichloromethane/methanol (19:1) for the elution. The product was recrystallized from diethyl ether. There was obtained 16 mg of (E)-5-(3,4-dichlorostyryl)-N-ethyl-2,3-dihydro-1H-1,4-benzodiazepine-1-carboxamide as an off-white solid. MS: m/e 387.9 [M+H]+.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue chromatographed on silica gel
  3. washfor the elution
  4. customThe product was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-f8ce97d52f20472381bd9e2ae734b734
Source dataset
uspto-grants-2004_03
Patent number
US06703387B2

Reaction notes

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