Potassium Hydroxide → N-butyltrifluoroacetyl-2,4-difluoroaniline

HRID 1494444Notes

Reaction equation

HRID 1494444 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH3:9])(=O)=O.[F:10][C:11]([F:24])([F:23])[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[F:22])=[O:13].[OH-].[K+]>CC(C)=O>[CH2:6]([N:14]([C:12](=[O:13])[C:11]([F:24])([F:23])[F:10])[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[F:22])[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 15953Butyl methanesulfonateHCID 4517860N-(2,4-difluorophenyl)-2,2,2-trifluoroacetamide

Product 1

HCID 54338454N-butyltrifluoroacetyl-2,4-difluoroanilineYield 53.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 60.8 g of n-butyl methanesulphonate and 22.5 g of trifluoroacetyl-2,4-difluoroaniline is dissolved in 50 ml of acetone at 40° C., and 22.4 g of KOH powder are added. The reaction mixture is kept at reflux for 30 minutes, filtered and evaporated on a rotary evaporator. The oily residue is rectified. 15 g of N-butyltrifluoroacetyl-2,4-difluoroaniline are obtained as a yellowish oil which distills at 106 - 110°/11.7 mbar.

Workup

  1. temperatureat reflux for 30 minutes
  2. filtrationfiltered
  3. customevaporated on a rotary evaporator

Sources & evidence

ORD record
ord-7f930598a23248f4aa016acf3a6999fc
Source dataset
uspto-grants-1991_06
Patent number
US05026625

Reaction notes

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