Thionyl Chloride → 4-[(2-methylbenzoyl)amino]benzoyl Chloride

HRID 439946

Reaction equation

HRID 439946 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=1)=[O:5].S(Cl)([Cl:22])=O>>[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([Cl:22])=[O:12])=[CH:9][CH:8]=1)=[O:5]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 116158144-[(2-methylbenzoyl)amino]benzoic Acid

Product 1

HCID 107074414-[(2-methylbenzoyl)amino]benzoyl Chloride

Procedure

A mixture of 10.3 g of 4-[(2-methylbenzoyl)amino]benzoic acid and 32 ml of thionyl chloride is refluxed for 1.5 hours. The solution is concentrated in vacuo. Toluene is added and the solvent removed in vacuo. Toluene is added and the mixture chilled and filtered to give the desired product as a yellow solid, 135°-141° C.

Workup

  1. temperatureis refluxed for 1.5 hours
  2. concentrationThe solution is concentrated in vacuo
  3. additionToluene is added
  4. customthe solvent removed in vacuo
  5. additionToluene is added
  6. temperaturethe mixture chilled
  7. filtrationfiltered

Sources & evidence

ORD record
ord-77a79c16614f4e92a5b0f2b18812fe41
Source dataset
uspto-grants-1996_05
Patent number
US05516774

Linked notes

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