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

HRID 1456180Notes

Reaction equation

HRID 1456180 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-35ecdf1ebb574c729af1e6cd8899527e
Source dataset
uspto-grants-1998_12
Patent number
US05843952

Reaction notes

Loading…