Dichloromethane → 2-Hydroxy-N-(1,2,2,2-tetrachloroethyl)benzamide

HRID 848063Notes

Reaction equation

HRID 848063 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].[Cl:17]CCl.S(Cl)(Cl)=O>CN(C)C=O>[Cl:17][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 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 2329832674-50-2

Product 1

HCID 129401702-Hydroxy-N-(1,2,2,2-tetrachloroethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

14.2 g of N-(1-hydroxy-2,2,2-trichloroethyl)-2-hydroxybenzamide was mixed with 100 ml of dichloromethane, 7.2 g of thionyl chloride and 0.1 g of N,N-dimethylformamide and the reaction was effected while stirring under reflux for three hours. The solvent was distilled off to obtain N-(1,2,2,2-tetrachloroethyl)-2-hydroxybenzamide (m.p.: 113°-113.5° C.). Without taking this out, 100 ml of dichloromethane and 3.8 g of iso-propyl mercaptan were added thereto and then 4.0 g of pyridine was also added dropwise. After effecting the reaction at room temperature for one hour, water was added thereto, the dichloromethane layer was separated out, dried and concentrated to obtain 16.2 g of N-(1-iso-propylthio-2,2,2-trichloroethyl)-2-hydroxybenzamide as white crystals.

Workup

  1. temperatureunder reflux for three hours
  2. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-c3badd86b64043d884bd0efa09f8ad8d
Source dataset
uspto-grants-1981_10
Patent number
US04294835

Reaction notes

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