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

HRID 375777Notes

Reaction equation

HRID 375777 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. Thionyl chloride (359.3 g, 3.02 moles) was added dropwise with stirring. After completion of the reaction, the solvent was removed by rotary evaporation affording a gray solid. The solid was crystallized from ethyl acetate to give 216 g of 4-dimethylaminobenzoyl chloride, yield 78%.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed by rotary evaporation
  3. customaffording a gray solid
  4. customThe solid was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-b121ad5c5ff34abc8be809134d9afed7
Source dataset
uspto-grants-1996_01
Patent number
US05487885

Reaction notes

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