Desmethylmedazepam → HCID 20333780, compound

HRID 1706611Notes

Reaction equation

HRID 1706611 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][CH:13]=3)[C:6]=2[CH:18]=1.[Cl:19][CH2:20][CH2:21][N:22]=[C:23]=[O:24]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:23]([NH:22][CH2:21][CH2:20][Cl:19])=[O:24])[CH2:10][CH2:9][N:8]=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[CH:18]=1

Participants

4

Reactant 2

HCID 15539DesmethylmedazepamHCID 160352-Chloroethyl isocyanate2×

Product 1

HCID 20333780HCID 20333780, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 parts of 7-chloro-2,3-dihydro-5-phenyl-1H-1,4-benzodiazepine is dissolved in 75 parts by volume of methylene chloride. To this solution is added 6 parts of 2-chloroethylisocyanate and the resultant mixture left standing at ambient temperature for about 48 hours. Then, additional 2 parts of 2-chloroethylisocyanate is added to the mixture, the mixture heated on a steam bath for about 4 hours and the solvent removed to give a solid. The solid is washed with ether and crystallized from a mixture of methylene chloride and hexane to give 7-chloro-N-(2-chloroethyl)-2,3-dihydro-5-phenyl-1H-1,4-benzodiazepine-1-carboxamide, as yellow crystals melting at about 160°-161° C. This compound is represented by the following formula ##STR17##

Workup

  1. temperaturethe mixture heated on a steam bath for about 4 hours
  2. customthe solvent removed
  3. customto give a solid
  4. washThe solid is washed with ether
  5. customcrystallized from a mixture of methylene chloride and hexane

Sources & evidence

ORD record
ord-53113fafce784d29b35f555a63c98364
Source dataset
uspto-grants-1980_06
Patent number
US04208327

Reaction notes

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