4-Chlorobenzoyl chloride → 4-chloro-N-(3-formylphenyl)benzamide

HRID 1696613

Reaction equation

HRID 1696613 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH:1][C:2]2[CH:9]=[CH:8][CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=2)=[O:16])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 74366Benzaldehyde, 3-amino-HCID 81531Diisopropylethylamine

Product 1

HCID 23750934-chloro-N-(3-formylphenyl)benzamideYield 129%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

to a solution of 242 mg of 3-aminobenzaldehyde (2 mmoles) and 250 μl of 4-chlorobenzoyl chloride (2 mmoles) in 5 ml of DMF is added 700 μl of DIEA (4 mmoles). The reaction is irradiated in under microwaves at 110° C. for 10 minutes. The precipitate formed is filtrated and washed with methanol. 670 mg of 4-Chloro-N-(3-formyl-phenyl)-benzamide are isolated as a white solid (yield=85%). Analytical LC/MS method A: ([M+H]+): 260

Workup

  1. customThe reaction is irradiated in under microwaves at 110° C. for 10 minutes
  2. customThe precipitate formed
  3. filtrationis filtrated
  4. washwashed with methanol

Sources & evidence

ORD record
ord-05054a6e1adc4eb8bca736275ffa08ab
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Linked notes

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