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

HRID 964717Notes

Reaction equation

HRID 964717 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.N1C=CC=CC=1.[C:18](Cl)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]>ClCCl>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 99644-(Trifluoromethyl)anilineHCID 62493Pivaloyl chloride

Product 1

HCID 2774289N-(4-(trifluoromethyl)phenyl)pivalamideYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4-trifluoromethylaniline (25 g, 0.155 mol) and pyridine (62 ml, 0.775 mol) in dichloromethane (300 ml) cooled to 0° C. under nitrogen was added dropwise pivaloyl chloride (19 ml, 0.155 mol). The reaction mixture was stirred at room temperature for 3.5 hr, then diluted with dichloromethane (300 ml). The resulting solution was washed sequentially with 1N aqueous hydrochloric acid solution (2×), saturated aqueous sodium bicarbonate solution, water and brine, dried (anhydrous sodium sulfate)and concentrated in vacuo to yield the title compound as a white solid (37 g, 97% yield).

Workup

  1. washThe resulting solution was washed sequentially with 1N aqueous hydrochloric acid solution (2×), saturated aqueous sodium bicarbonate solution, water and brine
  2. dry with materialdried (anhydrous sodium sulfate)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a9c72f4342da44e7b4c62ce9501bff6a
Source dataset
uspto-grants-1998_06
Patent number
US05770594

Reaction notes

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