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

HRID 1733954Notes

Reaction equation

HRID 1733954 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-c6430005549f42e9a6a58502ef80d970
Source dataset
uspto-grants-1996_07
Patent number
US05532235

Reaction notes

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