Ethanol → N-methyl-2-phenoxybenzamide

Temperature

0 °C

At 0° C., 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (22.4 g, 0.117 mol) was added to a solution of 2-phenoxybenzoic acid (25.0 g, 0.117 mol) and 1-hydroxybenzotrizole (15.8 g, 0.117 mmol) in DCM (80 ml) and N,N-dimethylformamide (160 ml). The reaction mixture was stirred for 20 min at 0° C. A 8.0 M solution of methylamine in ethanol (290 ml, 2.33 mol) was added. The reaction mixture was stirred for 16 hours at room temperature. It was diluted with ethyl acetate (200 ml) and washed with a 10% aqueous solution of sodium hydrogen sulphate (300 ml). The aqueous phase was extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogen carbonate 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 1:1 as eluent, to give 22.2 g of N-methyl-2-phenoxybenzamide.

1. stirringThe reaction mixture was stirred for 16 hours at room temperature
2. washwashed with a 10% aqueous solution of sodium hydrogen sulphate (300 ml)
3. extractionThe aqueous phase was extracted with ethyl acetate (3×100 ml)
4. washThe combined organic layers were washed with a saturated aqueous solution of sodium hydrogen carbonate
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 record

ord-61ceb5b90bd140afa4629d6537410d1f

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06437147B1