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

HRID 355829Notes

Reaction equation

HRID 355829 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 under vacuum. Toluene is added and the solvent removed under vacuum. Toluene is added and the mixture chilled and filtered to give a yellow solid, m.p. 135°-141° C.

Workup

  1. temperatureis refluxed for 1.5 hours
  2. concentrationThe solution is concentrated under vacuum
  3. additionToluene is added
  4. customthe solvent removed under vacuum
  5. additionToluene is added
  6. temperaturethe mixture chilled
  7. filtrationfiltered
  8. customto give a yellow solid, m.p. 135°-141° C.

Sources & evidence

ORD record
ord-3fedcfd2195441e7b8d0d1f2be5d5cee
Source dataset
uspto-grants-1998_11
Patent number
US05834461

Reaction notes

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