Triethylamine → N-[4-chloro-3-(trifluoromethyl)phenyl]-2,2-dimethylpropanamide

HRID 751071Notes

Reaction equation

HRID 751071 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].C(N(CC)CC)C.[C:20](Cl)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22]>C1COCC1>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:4][C:3]=1[C:9]([F:10])([F:11])[F:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 675744-Chloro-3-(trifluoromethyl)aniline

Product 1

HCID 715673N-[4-chloro-3-(trifluoromethyl)phenyl]-2,2-dimethylpropanamideYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of commercially available 4-chloro-3-(trifluoromethyl)aniline (15.0 g, 76.7 mmol) in anhydrous THF (200 mL) cooled to 0-5° C. was added triethylamine (11.7 mL, 84.4 mmol) followed by pivaloyl chloride (10.4 mL, 84.4 mmol) over 30 min. The ice bath was removed and the mixture stirred at rt for 1 h. The mixture was diluted with ether and filtered. The filtrate was washed with water (2×) and brine, dried (MgSO4), filtered and concentrated. The residue was triturated with hexanes and the solid was filtered and dried under vacuum to afford compound 18A (20.4 g, 95%); MS (ES) m/z 280 [M+1]+.

Workup

  1. customThe ice bath was removed
  2. additionThe mixture was diluted with ether
  3. filtrationfiltered
  4. washThe filtrate was washed with water (2×) and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated with hexanes
  9. filtrationthe solid was filtered
  10. customdried under vacuum

Sources & evidence

ORD record
ord-ea3426175d3f458bbb79cf7bf85de984
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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