Triethylamine → N-(4-(trifluoromethyl)phenyl)pivalamide

HRID 1171465Notes

Reaction equation

HRID 1171465 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(N(CC)CC)C.[C:19](Cl)(=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21]>C1C=CC=CC=1>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 99644-(Trifluoromethyl)anilineHCID 62493Pivaloyl chloride

Product 1

HCID 2774289N-(4-(trifluoromethyl)phenyl)pivalamideYield 88.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 4-trifluoromethylaniline (5 g, 0.031 mol) in 50 ml of dry benzene was added triethylamine (6.26 g, 8.63 ml, 0.06 mol) at 0° C. Pivaloyl chloride (4.5 g, 0.04 mol) was added slowly and stirred at RT over night. The RM was quenched with water and extracted with ethyl acetate. The organic layer was washed with water, brine and concentrated. To the solid was triturated with pet-ether and filtered to give N-(4-(trifluoromethyl)phenyl)-pivalamide (6.7 g) as white solid.

Workup

  1. customThe RM was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. concentrationconcentrated
  5. customTo the solid was triturated with pet-ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-cd9a629aaf9742379a48e10839ca324c
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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