Dimethylformamide → 3-Dimethylaminobenzoyl chloride hydrochloride

HRID 605247Notes

Reaction equation

HRID 605247 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](O)=[O:7].C(Cl)(=O)C([Cl:16])=O.CN(C=O)C>ClC(Cl)C>[ClH:16].[CH3:1][N:2]([CH3:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([Cl:16])=[O:7]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 668373-(Dimethylamino)benzoic acid

Product 1

HCID 227323093-Dimethylaminobenzoyl chloride hydrochlorideYield 124.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 3-(dimethylamino) benzoic acid (5.0 g. 30.0 mmol) in dichloroethane (50 mL) was added oxalyl chloride (5.6 g, 44.6 mmol) drop wise followed by catalytic amount of DMF. The reaction was stirred for 16 h. The excess oxalyl chloride and solvent were removed under reduced pressure. The residue was chased with benzene to give the desired product (6.1 g, 92%).

Workup

  1. customThe excess oxalyl chloride and solvent were removed under reduced pressure

Sources & evidence

ORD record
ord-5d75a835a4854f5189d6479b84c00620
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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