Ammonia → 2,2,3,3-Tetrafluoro-3-methoxypropanamide

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Reaction Steps

A solution of 140 g (0.74 mol) of methyl 3-methoxytetrafluoropropionate in 100 ml of ether was treated at 0° with 15.3 g (0.90 mol) of NH3. The resulting viscous mixture was stirred at 25° overnight and evaporated to dryness at 25° (10 mm). The crude residue was then recrystallized from ether/hexane to give 123.6 g (95%) of 3-methoxytetrafluoropropionamide, mp 78°-80°. An analytical sample was recrystallized from ether/hexane, m.p. 83° to 85°. IR (KBr): 2.95, 3.02 and 3.10 (NH2), 3.37 and 3.49 (sat'd CH), 5.92 (C=O), 6.19 (NH2), 7.5-10μ (CF, C--O). NMR ((CD3)2 (CO): 1H 6.67 (broad, 2H, NH2) and 3.66 ppm (s, 3H, OCH3): 19F -1.20.6 (t, JFF 4.7 Hz, 2F, CF2) and -121.8 ppm (t, JFF 4.7 Hz, of d, JHF, 2.1 Hz, 2F, CF2). Elemental analysis was consistent with the formula C4H5F4NO2. ##STR53##

Provenance & Evidence