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

HRID 55147Notes

Reaction equation

HRID 55147 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-08bfdbd7ef204255a26d113231fd2242
Source dataset
uspto-grants-1997_04
Patent number
US05624923

Reaction notes

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