Réaction #6521

Équation de réaction

water

pivaloyl chloride

3-trifluoromethyl-aniline

triethylamine

→

solid

Rendement 98.3%

2,2-Dimethyl-3'-Trifluoromethyl-Propionanilide

Rendement 98.3%

Solvants

ether

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ether (2×100 ml)
2. 2
   LavageThe combined ether extracts were washed successively with 0.5 HCl (100 ml)
3. 3
   SéchageThe ether solution was dried with MgSO4
4. 4
   Concentrationconcentrated in vacuo

Mode opératoire

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.

Source