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

HRID 1455337Notes

Reaction equation

HRID 1455337 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

Preparation B6, Step 1: 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-3417d077c0a3470badb4172d7e34675c
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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