Thionyl Chloride → 2-Hydroxy-N-(1,2,2,2-tetrachloroethyl)benzamide

HRID 848064Notes

Reaction equation

HRID 848064 reaction equation
O[CH:2]([NH:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])[C:3]([Cl:6])([Cl:5])[Cl:4].S(Cl)([Cl:19])=O>CN(C)C=O.ClCCl>[Cl:19][CH:2]([NH:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])[C:3]([Cl:6])([Cl:5])[Cl:4]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 2329832674-50-2

Product 1

HCID 129401702-Hydroxy-N-(1,2,2,2-tetrachloroethyl)benzamideYield 99.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To 14.2 g of N-(1-hydroxy-2,2,2-trichloroethyl)-2-hydroxybenzamide were added 100 ml of dichloromethane, 0.1 g of N,N-dimethylformamide and 7.2 g of thionyl chloride, and the reaction was effected while stirring under reflux for three hours. Excess thionyl chloride was distilled off together with the solvent under reduced pressure to obtain 15.1 g of N-(1,2,2,2-tetrachloroethyl)-2-hydroxybenzamide.

Workup

  1. temperatureunder reflux for three hours
  2. distillationExcess thionyl chloride was distilled off together with the solvent under reduced pressure

Sources & evidence

ORD record
ord-459cddabb48c419d843d31c9c199fd5e
Source dataset
uspto-grants-1981_10
Patent number
US04294835

Reaction notes

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