Thionyl Chloride → 3-Benzamidobenzoyl chloride

HRID 1696955Notes

Reaction equation

HRID 1696955 reaction equation
[C:1]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13](O)=[O:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:21])=O>C1(C)C=CC=CC=1>[C:1]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([Cl:21])=[O:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2566173-(benzoylamino)benzoic acid

Product 1

HCID 184700593-Benzamidobenzoyl chlorideYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1.5 g of 3-(benzoylamino)benzoic acid suspended in 10 ml of toluene was added 2 ml of thionyl chloride and the resulting mixture was stirred under a reflux condition for 2 hours. The reaction solution was returned to room temperature, and then the solvent was removed under a reduced pressure to obtain 1.53 g of the desired product (Yield: 95%) as a white solid.

Workup

  1. customwas returned to room temperature
  2. customthe solvent was removed under a reduced pressure

Sources & evidence

ORD record
ord-394df36d5b8a4cd487c4e2e51b31f491
Source dataset
uspto-grants-2012_04
Patent number
US08163804B2

Reaction notes

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