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

HRID 2050171Notes

Reaction equation

HRID 2050171 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>C1C=CC=CC=1>[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

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2329832674-50-2

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2,500 ml of benzene was added to 1,423 g of N-(1'-hydroxy-2',2',2'-trichloroethyl)-2-hydroxy benzamide and then 833 g of thionyl chloride was added thereto and heated under reflux at 70°-80° C. for 4 hours to obtain N-(1',2',2',2'-tetrachloroethyl)-2-hydroxy benzamide (white crystal, melting point of 113°-113.5° C., Anal. Found: C,35.74; H,2.12; N,4.70 Calcd. for C9H7Cl4NO2 : C,35.68; H,2.33; N,4.62 and the resultant reaction mixture, without separation of the crystals, was cooled to below 30° C. and mixed with 1,250 g of methanol and heated under reflux for 2 hours at 55°-60° C. followed by removing the solvent and the residue was poured into water, filtered and dried to obtain 1,380 g (yield 92.4%) white crystals of N-(1'-methoxy-2',2',2'-trichloroethyl)-2-hydroxy benzamide.

Workup

  1. temperatureheated
  2. temperatureunder reflux at 70°-80° C. for 4 hours

Sources & evidence

ORD record
ord-59dbc18478c14be69b91dd55cabaec81
Source dataset
uspto-grants-1980_04
Patent number
US04200632

Reaction notes

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