Bromoacetyl chloride → 1-bromomethyl-8-chloro-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine

HRID 596358Notes

Reaction equation

HRID 596358 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][NH2:13])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:20]=1.[Br:21][CH2:22][C:23](Cl)=O.C([O-])(=O)C.[Na+]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:23]([CH2:22][Br:21])=[N:13][N:12]=[C:10]3[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:20]=1

Participants

4

Reactant 3

HCID 89602Bromoacetyl chlorideHCID 517045Sodium AcetateHCID 123908747-Chloro-2-hydrazinyl-5-phenyl-3H-1,4-benzodiazepine

Product 1

HCID 202052201-bromomethyl-8-chloro-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Procedure

In the manner given in Preparation 10, 7-chloro-5-phenyl-3H-1,4-benzodiazepine-2-yl hydrazine is reacted with bromoacetyl chloride and after 1.5 hours with sodium acetate, then refluxed to give 8-chloro-1-(bromomethyl)6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine. Preparation 12 8-Fluoro-1-(Chloromethyl)-6-(o-fluorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Workup

  1. temperaturerefluxed

Sources & evidence

ORD record
ord-9771980c580344c585c00cf179f45550
Source dataset
uspto-grants-1977_03
Patent number
US04010177

Reaction notes

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