Bromoacetyl bromide → 8-nitro-1(bromomethyl)-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a]-[1,4]benzodiazepine

HRID 596361Notes

Reaction equation

HRID 596361 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:13]=[C:12]([NH:14][NH2:15])[CH2:11][N:10]=[C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:8]=2[CH:23]=1)([O-:3])=[O:2].[Br:24][CH2:25][C:26](Br)=O.C([O-])(=O)C.[Na+]>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:13]3[C:26]([CH2:25][Br:24])=[N:15][N:14]=[C:12]3[CH2:11][N:10]=[C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:8]=2[CH:23]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 61147Bromoacetyl bromideHCID 517045Sodium AcetateHCID 202918567-nitro-2-hydrazino-5-(o-chlorophenyl)-3H-1,4-benzodiazepine

Product 1

HCID 202918328-nitro-1(bromomethyl)-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a]-[1,4]benzodiazepine

Procedure

In the manner given in Preparation 10, 7 -nitro-5(o-chlorophenyl)-3H-1,4-benzodiazepin-2-yl hydrazine is reacted with bromoacetyl bromide and after 1.5 hours with sodium acetate, then refluxed to give 8-nitro-1(bromomethyl)-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a]-[1,4]benzodiazepine. Preparation 15 1-(Chloromethyl)-7-(trifluoromethyl)-6-(o-fluorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Workup

  1. temperaturerefluxed

Sources & evidence

ORD record
ord-c93ba8c0dfd54863b34ca9a4668b6d4f
Source dataset
uspto-grants-1977_03
Patent number
US04010177

Reaction notes

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