4-(Dimethylamino)benzoic acid → 4-(Dimethylamino)benzoyl chloride

HRID 1954647Notes

Reaction equation

HRID 1954647 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1.S(Cl)([Cl:15])=O>C(OCC)(=O)C>[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:15])=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 120924-(Dimethylamino)benzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 44007824-(Dimethylamino)benzoyl chlorideYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Dimethylaminobenzoic acid (250 g, 1.51 moles) was suspended in 2 L of ethyl acetate and thionyl chloride (359.3 g, 3.02 moles) was added. After the completion, the solvent was evaporated. Crystallization from ethyl acetate gave 216 g of 4-dimethylaminobenzoyl chloride (78%).

Workup

  1. customAfter the completion, the solvent was evaporated
  2. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-3e283784c5244d3e8ca04569ded167bf
Source dataset
uspto-grants-2000_09
Patent number
US06123928

Reaction notes

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