Water → 7-chloro-N-(2-chloroethyl)-5-(o-chlorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine-1-carboxamide 4-oxide

HRID 1706615Notes

Reaction equation

HRID 1706615 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12]([NH:14][CH2:15][CH2:16][Cl:17])=[O:13])[CH2:10][CH2:9][N:8]=[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:6]=2[CH:25]=1.[OH2:26]>C(O)(=O)C.C(OO)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12]([NH:14][CH2:15][CH2:16][Cl:17])=[O:13])[CH2:10][CH2:9][N+:8]([O-:26])=[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:6]=2[CH:25]=1

Participants

5

Reactant 2

HCID 962WaterHCID 20333751HCID 20333751, compound

Product 1

HCID 203337717-chloro-N-(2-chloroethyl)-5-(o-chlorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine-1-carboxamide 4-oxide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6585Peracetic AcidSolvent

Procedure

10 Parts of 7-chloro-N-(2-chloroethyl)-5-(o-chlorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine-1-carboxamide is dissolved in 50 parts by volume of glacial acetic acid and to this solution 10 parts by volume of 40% peracetic acid is added all at once with stirring. The reaction mixture is stirred at ambient temperature for about 24 hours and then slowly poured into 1000 parts by volume of cold water. The precipitate which forms is extracted with methylene chloride, the extract dried over magnesium sulfate and the solvent removed. The residue crystallizes from ethanol to afford 7-chloro-N-(2-chloroethyl)-5-(o-chlorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine-1-carboxamide 4-oxide. This compound is represented by the following formula ##STR37##

Workup

  1. additionis added all at once
  2. stirringThe reaction mixture is stirred at ambient temperature for about 24 hours
  3. extractionThe precipitate which forms is extracted with methylene chloride
  4. dry with materialthe extract dried over magnesium sulfate
  5. customthe solvent removed
  6. customThe residue crystallizes from ethanol

Sources & evidence

ORD record
ord-d7ec9b7d409e4e5e9553896633efeee1
Source dataset
uspto-grants-1980_06
Patent number
US04208327

Reaction notes

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