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

HRID 722345Notes

Reaction equation

HRID 722345 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:19][C:20]([CH3:25])([CH3:24])[C:21](Cl)=[O:22]>ClCCl>[F:11][C:8]([F:9])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:21](=[O:22])[C:20]([CH3:25])([CH3:24])[CH3:19])=[CH:3][CH:4]=1

Participants

5

Reactant 3

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

Product 1

HCID 2774289N-(4-(trifluoromethyl)phenyl)pivalamideYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of dichloromethane (200 mL), 4-aminobenzotrifluoride (32.0 g, 199 mmol) and triethylamine (40 g, 396 mmol) was cooled to 0° C under a dry nitrogen atmosphere. Trimethylacetyl chloride (32.9 g, 273 mmol) was added drop-wise over 2 hours, maintaining the temperature below 10° C. After the addition, the contents were allowed to warm to room temperature for 2 hours. The reaction was washed with water (2×200 mL), saturated ammonium chloride solution (2×200 mL), dried over sodium sulfate and filtered. The solvent was removed in vacuo to afford a white solid, N-(4-trifluoromethylphenyl)-2,2-dimethylpropanamide (48.0 g, 98%): mp 157–159° C. 1H NMR (CDCl3/300 MHz) 7.61 (ab, 4H, J=8.7, Δν=28.6 Hz), 7.47 (br s, 1H), 1.33 (s, 9H). ESHRMS m/z 246.1123 (M+H+, Calc'd 246.1106). Anal. Calc'd for C12H11F3NO: C, 58.77; H, 5.75; N, 5.71. Found: C, 58.28; H, 5.79; N, 5.65.

Workup

  1. temperaturemaintaining the temperature below 10° C
  2. additionAfter the addition
  3. washThe reaction was washed with water (2×200 mL), saturated ammonium chloride solution (2×200 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c39238dae3e74c1494774054e75ec5d6
Source dataset
uspto-grants-2006_11
Patent number
US07138411B2

Reaction notes

Loading…