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

HRID 2279244Notes

Reaction equation

HRID 2279244 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].CCN(CC)CC.[C:20](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])=[O:21]>C1COCC1.O>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:20](=[O:21])[C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:4][C:3]=1[C:9]([F:10])([F:11])[F:12]

Participants

6

Reactant 3

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

Product 1

HCID 715673N-[4-chloro-3-(trifluoromethyl)phenyl]-2,2-dimethylpropanamideYield 63.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-3-(trifluoromethyl) aniline (3a) (0.5 g, 2.55 mmol) in dry THF (8 mL), cooled to 0° C., Et3N (0.4 mL, 2.76 mmol) followed by PivCl (0.34 mL, 2.8 mmol) were added. The reaction mixture was stirred at room temperature for 4 h. After completion of reaction (by TLC), the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (3×15 mL). The combined organic extracts were washed with water (30 mL). The organic layer was separated dried over Na2SO4 and concentrated under reduced pressure to give the crude material which was triturated with n-hexane to afford the desired amide 3b (0.45 g, 60%) as a white solid.

Workup

  1. additionwere added
  2. customAfter completion of reaction (by TLC)
  3. extractionextracted with EtOAc (3×15 mL)
  4. washThe combined organic extracts were washed with water (30 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude material which
  9. customwas triturated with n-hexane

Sources & evidence

ORD record
ord-f13cefe71a1143008cb1a7574a284a5f
Source dataset
uspto-grants-2015_09
Patent number
US09133182B2

Reaction notes

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