Bromoacetyl bromide → N-(4-isopropoxycarbonylamino-2-nitrophenyl)-2-bromoacetamide

HRID 1415640Notes

Reaction equation

HRID 1415640 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[CH:6]([O:9][C:10]([NH:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1)=[O:11])([CH3:8])[CH3:7]>C1(C)C=CC=CC=1>[CH:6]([O:9][C:10]([NH:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:3](=[O:4])[CH2:2][Br:1])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1)=[O:11])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 61147Bromoacetyl bromideHCID 126780374-Isopropoxycarbonylamino-2-nitroaniline

Product 1

HCID 21483033N-(4-isopropoxycarbonylamino-2-nitrophenyl)-2-bromoacetamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Bromoacetyl bromide (18.6 g) was added dropwise with stirring to a solution of 4-isopropoxycarbonylamino-2-nitroaniline (22g) in toluene (300 ml). The solution was refluxed for 1 hour, cooled, and the solid filtered off and recrystallised from benzene to give N-(4-isopropoxycarbonylamino-2-nitrophenyl)-2-bromoacetamide (20 g), m.p. 195°-197° C.

Workup

  1. temperatureThe solution was refluxed for 1 hour
  2. temperaturecooled
  3. filtrationthe solid filtered off
  4. customrecrystallised from benzene

Sources & evidence

ORD record
ord-56c4ff46aca943199cdfedec9b678a34
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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