Ethanol → N-methyl-2-(3-trifluoromethylphenyl)acetamide

Temperatur

0 °C

At 0° C., 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (21.6 g (0.11 mol) was added to a solution of 3-(trifluoromethyl)phenylacetic acid (Aldrich 19,335-6, 23.0 g, 0.11 mol) and 1-hydroxybenzothiazole (21.6 g, 0.11 mol) in DCM (50 ml) and N,N-dimethylformamide (50 ml). The reaction mixture was stirred for 20 min at 0° C. A 33% solution of methylamine in ethanol (280 ml, 2.25 mol) was added. The reaction mixture was stirred for 56 hours and successively diluted with ethyl acetate (200 ml). It was washed with a 10% aqueous solution of sodium hydrogensulphate (300 ml). The aqueous phase was extracted with ethyl acetate (2×150 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (300 ml) and dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (300 g), using ethyl acetate/heptane 2:1 as eluent, to give 19.8 g of N-methyl-2-(3-trifluoromethylphenyl)acetamide.

1. stirringThe reaction mixture was stirred for 56 hours
2. washIt was washed with a 10% aqueous solution of sodium hydrogensulphate (300 ml)
3. extractionThe aqueous phase was extracted with ethyl acetate (2×150 ml)
4. washThe combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (300 ml)
5. dry with materialdried over magnesium sulphate
6. customThe solvent was removed in vacuo
7. customThe crude product was purified by flash chromatography on silica (300 g)

ORD-Eintrag

ord-7a39eb99ff8d46ba8c0ddbdd53a53c2f

Quelldatensatz

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06437147B1