4-(Trifluoromethyl)aniline → N-(4-(trifluoromethyl)phenyl)pivalamide

HRID 34628Notes

Reaction equation

HRID 34628 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[C:12](Cl)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14].C(=O)(O)[O-].[Na+]>ClCCl>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 99644-(Trifluoromethyl)anilineHCID 62493Pivaloyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 2774289N-(4-(trifluoromethyl)phenyl)pivalamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6.87 g (0.043 mol) of 4-trifluoromethylaniline in 110 ml of dichloromethane was added 5.25 ml (0.043 mol) of pivaloylchloride. After stirring for 1.5 hours, 190 ml of a saturated solution of aqueous sodium bicarbonate was added. The reaction proceeded an additional 2 hours and the organic layer was separated and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed to give the title compound, yield 9.16 g (88%), m.p. 154°-158° C.

Workup

  1. waitThe reaction proceeded an additional 2 hours
  2. customthe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe solution was filtered
  5. customthe solvent removed

Sources & evidence

ORD record
ord-46561eed4dc941348df7ba05d11138e9
Source dataset
uspto-grants-1988_08
Patent number
US04762838

Reaction notes

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