反应详情

To a 100 mL pressure vessel with a stirring bar was added ethyl 4-(1,1-dimethylethoxycarbonyl)amino-3-methylphenoxyacetate (1.00 g, 3.24 mmol). The vessel was cooled in a Dry Ice®/2-propanol bath to -78° C. and dimethylamine was condensed onto the solid to a final volume of ~30 mL. The reaction vessel was sealed, allowed to warm to ambient temperature and stirred for 13 days. The excess dimethylamine was vented and the residue was dissolved in CHCl3 and concentrated, twice to remove the last traces of dimethylamine. The crude product was chromatographed on 75 g of silica gel using 75/25 EtOAC-hexane as eluant to provide 1 g (100% yield) N,N-dimethyl-4-(1,1-dimethylethoxycarbonyl)amino-3-methylphenoxyacetamide as a white, crystalline solid. 1H NMR (CDCl3): d 1.50 (s, 9H), 2.22 (s, 3H), 2.96 (s, 3H), 3.07 (s, 3H), 4.63 (s, 2H), 6.09 (br s, 1H), 6.77, (s, 2H), 7.52 (br s, 1H). ##STR51## N,N-Dimethyl 4-amino-3-methylphenoxyacetamide (5-3)

1. customcondensed onto the solid to a final volume of ~30 mL
2. customThe reaction vessel was sealed
3. concentrationconcentrated
4. customtwice to remove the last traces of dimethylamine
5. customThe crude product was chromatographed on 75 g of silica gel using 75/25 EtOAC-hexane as eluant