Chloride → 4-(Dimethylamino)benzoyl chloride

HRID 1075658Notes

Reaction equation

HRID 1075658 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.[Cl-].S(Cl)([Cl:16])=O>>[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:16])=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 312ChlorideHCID 120924-(Dimethylamino)benzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 44007824-(Dimethylamino)benzoyl chloride

Procedure

Firstly, 4-dimethylamino benzoylchloride was prepared. The reaction was accomplished by placing 4-dimethylamino benzoic acid (ex. Lancaster) (4.0 g, 24.22 mmol) in a 25 ml round bottom flask, to which was added thoinyl chloride (ex. Aldrich) (3.0 ml). This reaction mixture became orange immediately upon the addition of the thionyl chloride. The reaction mixture was stirred for 1 hour at ambient temperature, after which time the remaining thionyl chloride was removed under reduced pressure. The last trace of the thionyl chloride was removed by azeotroping with dry benzene (2×20 ml).

Workup

  1. customafter which time the remaining thionyl chloride was removed under reduced pressure
  2. customThe last trace of the thionyl chloride was removed
  3. customby azeotroping with dry benzene (2×20 ml)

Sources & evidence

ORD record
ord-4e5d6948645f4787b3c181066a08235f
Source dataset
uspto-grants-1999_05
Patent number
US05905164

Reaction notes

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