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

HRID 1625655Notes

Reaction equation

HRID 1625655 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>O1CCCC1>[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 chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 1000 mL round bottomed flask was added 4-dimethylamino-benzoic acid (50.0 g, 1.0 eq) and THF (600 mL). A solution of thionyl chloride (44.16 mL, 2.0 eq) in tetrahydrofuran was added and the resulting mixture heated to reflux for 4 hours. The excess thionyl chloride and solvent were removed under reduced pressure to yield 4-dimethylamino-benzoyl chloride as a solid, which was used without further purification in the preparation of compound 560.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureto reflux for 4 hours
  3. customThe excess thionyl chloride and solvent were removed under reduced pressure

Sources & evidence

ORD record
ord-80c6c61fd2ba4389a778961610f73753
Source dataset
uspto-grants-2014_07
Patent number
US08785381B2

Reaction notes

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