Thionyl Chloride → N-chloromethyl-2-(trifluoromethyl)benzamide

HRID 56042Notes

Reaction equation

HRID 56042 reaction equation
O[CH2:2][NH:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([F:14])([F:13])[F:12].S(Cl)([Cl:18])=O>ClCCl>[Cl:18][CH2:2][NH:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([F:14])([F:13])[F:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68429331N-(Hydroxymethyl)-2-(trifluoromethyl)benzamide

Product 1

HCID 118071537N-chloromethyl-2-(trifluoromethyl)benzamideYield 100.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 15.50 g of N-hydroxymethyl-2-(trifluoromethyl)benzamide in 200 ml of dichloromethane, 16.83 g of thionyl chloride was added dropwise with stirring under cooling with ice, and after the addition, the mixture was stirred at room temperature for another 3 hours. After completion of the reaction, the solvent was evaporated under reduced pressure, and the precipitated solid was washed with 50 ml of hexane to obtain 16.90 g of the desired product as white crystals.

Workup

  1. temperatureunder cooling with ice
  2. additionafter the addition
  3. stirringthe mixture was stirred at room temperature for another 3 hours
  4. customAfter completion of the reaction
  5. customthe solvent was evaporated under reduced pressure
  6. washthe precipitated solid was washed with 50 ml of hexane

Sources & evidence

ORD record
ord-1fee9fa51097432dafd8511e36610e76
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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