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

HRID 1846310Notes

Reaction equation

HRID 1846310 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>CN(C=O)C>[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

4

Reactant 2

HCID 78074-BromoanilineHCID 8359Isatoic Anhydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of isatoic anhydride (4.00 g, 24.5 mmol) and 4-bromoaniline (4.20 g, 24.5 mmol) in anhydrous DMF (30 mL) was stirred at 115° C. for 60 hours under nitrogen. DMF was removed under vacuum and the residue was partitioned between ethyl acetate (75 mL) and water (75 mL). The organic phase was separated, washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under vacuum to give crude 2-amino-N-(4-bromophenyl)benzamide. Yield: 1.00 g (14%).

Workup

  1. customDMF was removed under vacuum
  2. customthe residue was partitioned between ethyl acetate (75 mL) and water (75 mL)
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-e59c02f740e24d44aef78818e1b58d43
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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