Bromoacetyl bromide → HCID 21482995, compound

HRID 1415646Notes

Reaction equation

HRID 1415646 reaction equation
[CH2:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH2:2][CH2:3][CH3:4].[Br:15][CH2:16][C:17](Br)=[O:18]>C1(C)C=CC=CC=1>[CH2:1]([C:5]1[CH:11]=[CH:10][C:8]([NH:9][C:17](=[O:18])[CH2:16][Br:15])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 61147Bromoacetyl bromideHCID 77229Benzenamine, 4-butyl-2-nitro-

Product 1

HCID 21482995HCID 21482995, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-n-butyl-2-nitroaniline (29.1 g) in toluene (100 ml) was treated with bromoacetyl bromide (33.3 g). The mixture was boiled under reflux for 3/4 hour and the toluene evaporated off. The residual oil was poured into petroleum spirit (b.p. 60°-80° C; 400 ml). Crystals were deposited and these were removed by filtration to give N-(4-n-butyl-2-nitrophenyl)-2-bromoacetamide (41 g), m.p. 56°-57° C.

Workup

  1. temperatureunder reflux for 3/4 hour
  2. customthe toluene evaporated off
  3. additionThe residual oil was poured into petroleum spirit (b.p. 60°-80° C; 400 ml)
  4. customthese were removed by filtration

Sources & evidence

ORD record
ord-34f540d0d41d41dbb854a8055330ba82
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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