4-Bromoaniline → 2-amino-n-(4-bromophenyl)benzamide

HRID 1846263Notes

Reaction equation

HRID 1846263 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.[Br:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1>>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:18][C:17]1[CH:19]=[CH:20][C:14]([Br:13])=[CH:15][CH:16]=1)=[O:4]

Participants

3

Reactant 2

HCID 78074-BromoanilineHCID 8359Isatoic Anhydride

Product 1

HCID 4788192-amino-n-(4-bromophenyl)benzamide

Conditions

Temperature
130 °C

Procedure

1H-Benzo[d][1,3]oxazine-2,4-dione (A) (3.26 g, 20.0 mmol) and 4-bromo-aniline (H) (3.23 g, 18.8 mmol) were mixed together as a neat mixture (both solids), and the reaction mixture was stirred at 130° C. for 4 hours, and then cooled to room temperature. The crude compound was purified by the Simpliflash system (20% ethyl acetate in hexanes as eluent) to give 2-amino-N-(4-bromo-phenyl)-benzamide (J) as white solid. Yield: 4.35 g (75%).

Workup

  1. temperaturecooled to room temperature
  2. customThe crude compound was purified by the Simpliflash system (20% ethyl acetate in hexanes as eluent)

Sources & evidence

ORD record
ord-f4ba447f34f54229bcccae17d5f2c310
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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