Chloroacetyl isocyanate → 7-chloro-N-chloracetyl-5-(o-chlorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine-1-carboxamide

HRID 1706613Notes

Reaction equation

HRID 1706613 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][N:8]=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[C:6]=2[CH:19]=1.[Cl:20][CH2:21][C:22]([N:24]=[C:25]=[O:26])=[O:23]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:25]([NH:24][C:22](=[O:23])[CH2:21][Cl:20])=[O:26])[CH2:10][CH2:9][N:8]=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[C:6]=2[CH:19]=1

Participants

4

Reactant 2

HCID 78209Chloroacetyl isocyanateHCID 20333776HCID 20333776, compound

Product 1

HCID 203337737-chloro-N-chloracetyl-5-(o-chlorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of 8 parts of 7-chloro-5-(o-chlorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine, 4.9 parts of chloroacetylisocyanate, and 200 parts by volume of methylene chloride is stirred under nitrogen atmosphere at ambient temperature for about one hour. The mixture is then filtered through a layer of activated magnesium silicate and the filtrate evaporated to dryness. The resultant yellow oil is dissolved in ether and the solvent removed by evaporation to give gummy residue which upon crystallization from ether affords 7-chloro-N-chloracetyl-5-(o-chlorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine-1-carboxamide, as a yellow solid melting at about 152°-156° C. This compound is represented by the following formula ##STR21##

Workup

  1. filtrationThe mixture is then filtered through a layer of activated magnesium silicate
  2. customthe filtrate evaporated to dryness
  3. dissolutionThe resultant yellow oil is dissolved in ether
  4. customthe solvent removed by evaporation
  5. customto give gummy residue which
  6. customupon crystallization from ether

Sources & evidence

ORD record
ord-380e3946dc8e4869a061b8e7e1e53b64
Source dataset
uspto-grants-1980_06
Patent number
US04208327

Reaction notes

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