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

HRID 1415648Notes

Reaction equation

HRID 1415648 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=1)=[O:4].[Br:16][CH2:17][C:18](Br)=[O:19]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:12]=[CH:11][C:9]([NH:10][C:18](=[O:19])[CH2:17][Br:16])=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 61147Bromoacetyl bromideHCID 214830664-Methoxycarbonylamino-2-nitroaniline

Product 1

HCID 21483050N-(4-methoxycarbonylamino-2-nitrophenyl)-2-bromoacetamideYield 63.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

4-Methoxycarbonylamino-2-nitroaniline (30 g) was dissolved in toluene (300 ml) and the solution treated with bromoacetyl bromide (28.7 g). The mixture was refluxed for 3 hours and toluene (300 ml) was added. The hot mixture was filtered and the filtrate allowed to cool to give N-(4-methoxycarbonylamino-2-nitrophenyl)-2-bromoacetamide (30 g), m.p. 160°-162° C.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. filtrationThe hot mixture was filtered
  3. temperatureto cool

Sources & evidence

ORD record
ord-369669b83ea24703a65500d34048beba
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

Loading…