Water → 2,2-Dimethyl-n-[3-(trifluoromethyl)phenyl]propanamide

HRID 6425

Reaction equation

HRID 6425 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[F:8][C:9]([F:18])([F:17])[C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][CH:16]=1)[NH2:13].C(N(CC)CC)C.O>CCOCC>[CH3:3][C:2]([CH3:5])([CH3:4])[C:1]([NH:13][C:12]1[CH:14]=[CH:15][CH:16]=[C:10]([C:9]([F:8])([F:17])[F:18])[CH:11]=1)=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 73753-(Trifluoromethyl)anilineHCID 8471TriethylamineHCID 62493Pivaloyl chloride

Product 1

HCID 7143392,2-Dimethyl-n-[3-(trifluoromethyl)phenyl]propanamideYield 98.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of pivaloyl chloride (3.62 g; 30 mmol) in 40 ml dry ether was added dropwise at room temperature to a mixture of 3-trifluoromethyl-aniline (4.83 g, 30 mmol) and triethylamine (4.25 ml, 30.5 mmol). This was stirred at room temperature for a period of 14 hours and then poured into 200 ml water, extracted with ether (2×100 ml). The combined ether extracts were washed successively with 0.5 HCl (100 ml); water (2×50 ml); 7% KOH (100 ml) and water (2×50 ml). The ether solution was dried with MgSO4 and concentrated in vacuo to give a white solid (7.23 gm, 98%, m.p. 112.5° C.). The 2,2-dimethyl-3'-trifluoromethyl-propionanilide was recrystallized with dichloromethane and petroleum ether mixture.

Workup

  1. extractionextracted with ether (2×100 ml)
  2. washThe combined ether extracts were washed successively with 0.5 HCl (100 ml)
  3. dry with materialThe ether solution was dried with MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6cab89fbffc94bf8aa8d99d718c666ee
Source dataset
uspto-grants-1993_09
Patent number
US05248781

Linked notes

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