Thionyl Chloride → N-[2,6-dimethyl-4-{1-chloro-2,2,2-trifluoro-1-(trifluoromethyl)ethyl}phenyl]3-(benzoylamino)benzamide

HRID 2371004Notes

Reaction equation

HRID 2371004 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8](O)([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([CH3:18])[C:3]=1[NH:19][C:20](=[O:36])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([NH:27][C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:22]=1.S(Cl)([Cl:39])=O>N1C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([Cl:39])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([CH3:18])[C:3]=1[NH:19][C:20](=[O:36])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([NH:27][C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:22]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23150030N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl) ethyl}phenyl]3-(benzoylamino)benzamide

Product 1

HCID 23150009N-[2,6-dimethyl-4-{1-chloro-2,2,2-trifluoro-1-(trifluoromethyl)ethyl}phenyl]3-(benzoylamino)benzamideYield 75%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

At room temperature, 8.0 g of N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl}phenyl] 3-(benzoylamino)benzamide and 1.0 g of pyridine were introduced to 40 ml of thionyl chloride. Then, the temperature was elevated, and the mixture was stirred under reflux conditions. After the loss of the starting material was confirmed through TLC, the reaction solution was cooled and was concentrated under reduce pressure. Thus obtained residue was purified by silica gel chromatography (eluent:hexane:ethyl acetate=3:1) to give 6.2 g (yield 75%) of the title compound as a powder form.

Workup

  1. temperaturethe reaction solution was cooled
  2. concentrationwas concentrated
  3. customThus obtained residue was purified by silica gel chromatography (eluent:hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-03c06792ff9540a3a300a8257dd1b443
Source dataset
uspto-grants-2014_04
Patent number
US08710234B2

Reaction notes

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