Water → HCID 22467517, compound

HRID 1934718Notes

Reaction equation

HRID 1934718 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][NH2:6].[Br:12][C:13]1[CH:24]=[C:17]2[C:18](OC(=O)[NH:22][C:16]2=[CH:15][CH:14]=1)=[O:19].O.C(OCC)(=O)C>CN(C)C=O>[NH2:22][C:16]1[CH:15]=[CH:14][C:13]([Br:12])=[CH:24][C:17]=1[C:18]([NH:6][CH2:5][C:4]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:2]([Cl:1])[CH:3]=1)=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2885615-Bromoisatoic AnhydrideHCID 7380383-Chloro-4-methoxybenzylamine

Product 1

HCID 22467517HCID 22467517, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-chloro-4-methoxybenzylamine (234 mg) in N,N-dimethylformamide (5 mL) was added dropwise to a solution of 5-bromoisatoic anhydride (300 mg) in N,N-dimethylformamide (3 mL). The reaction mixture was stirred for an hour at ambient temperature. The mixture was poured into a mixture of water and ethyl acetate. The precipitates were collected by filtration and washed with 2-propanol to give 2-amino-5-bromo-N-(3-chloro-4-methoxybenyl)benzamide (245 mg) as white powders.

Workup

  1. filtrationThe precipitates were collected by filtration
  2. washwashed with 2-propanol

Sources & evidence

ORD record
ord-eba35c364eed45e6ab1d44868c1f7a9a
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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