Carbon Tetrachloride → 2-Hydroxy-N-(1,2,2,2-tetrachloroethyl)benzamide

HRID 848058Notes

Reaction equation

HRID 848058 reaction equation
S(Cl)(Cl)=O.O[CH:6]([NH:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19])[C:7]([Cl:10])([Cl:9])[Cl:8].C(Cl)(Cl)(Cl)[Cl:22]>CN(C)C=O>[Cl:22][CH:6]([NH:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19])[C:7]([Cl:10])([Cl:9])[Cl:8]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 24386Thionyl ChlorideHCID 2329832674-50-2

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5 g of thionyl chloride was added dropwise to the mixture of 10 g of N-(1-hydroxy-2,2,2-trichloroethyl)-2-hydroxybenzamide, 50 ml of carbon tetrachloride and 0.1 g of N,N-dimethylformamide under stirring. After effecting the reaction under reflux for one hour, the solvent was distilled off under reduced pressure to obtain N-(1,2,2,2-tetrachloroethyl)-2-hydroxybenzamide (m.p.: 113°-113.5° C.). Without taking out the compound thus resulted, thereto were added 50 ml of acetone and also 7.2 g of octyl thioglycolate (n), and the mixture was stirred at room temperature for one hour. The solvent was distilled off and the rest was purified by silica gel column chromatography to obtain 3.0 g of N-(1-n-octyloxycarbonylmethylthio-2,2,2-trichloroethyl)-2-hydroxybenzamide as a light yellow oily substance. nD25 1.5031

Workup

  1. customthe reaction
  2. temperatureunder reflux for one hour
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4499cafb62364ccaa8c067aaf3ca182b
Source dataset
uspto-grants-1981_10
Patent number
US04294835

Reaction notes

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