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

HRID 965327Notes

Reaction equation

HRID 965327 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.C(Cl)(=O)C([Cl:16])=O>C1(C)C=CC=CC=1>[CH3:1][N:2]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:16])=[O:8])=[CH:5][CH:4]=1)[CH3:12]

Participants

4

Reactant 2

HCID 120924-(Dimethylamino)benzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 44007824-(Dimethylamino)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a round bottom flask fitted with a reflux condenser is placed 4 g of p-dimethylaminobenzoic acid and 8 ml of oxalylchloride. The evolution of gas starts immediately and the spontaneous reaction is run at room temperature for 15 minutes. 8 ml of toluene is added and and the mixture is heated to gentle reflux for one hour. The reaction mixture is then distilled to dryness under reduced pressure to produce a blue-green solid which is washed with ether and dried on a watch glass.

Workup

  1. customIn a round bottom flask fitted with a reflux condenser
  2. customThe evolution of gas starts immediately and the spontaneous reaction
  3. temperaturethe mixture is heated
  4. temperatureto gentle reflux for one hour
  5. distillationThe reaction mixture is then distilled to dryness under reduced pressure
  6. customto produce a blue-green solid which
  7. washis washed with ether
  8. customdried on a watch glass

Sources & evidence

ORD record
ord-93ed12975706473e834d1a902029f516
Source dataset
uspto-grants-1998_06
Patent number
US05773592

Reaction notes

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