Hydrochloric Acid → N-(3-Chloro-3-methyl-2-nitrosobutyl)-5-nitro-2-furancarboxamide

Participants

Reaction Conditions

Reaction Steps

N-(3-Methyl-2-butenyl)-5-nitro-2-furancarboxamide (2.2 g, 0.01 mol) was suspended in isoamyl nitrite (60 mL) and cooled to -5° C. concentrated HCl (1 mL, 37%, 0.01 mol) was added through a syringe. The reaction mixture was stirred at -5° C. for 30 min and at room temperature for 30 min. The solid was filtered and washed with chilled (-10° C.) ethanol-ether (100 mL). A light green powder was obtained. Yield: 1.5 g (52%). mp 110°-112° C. MS m/z 254 [(M+H)-HCl]+. 1H NMR (DMSO-d6) ε 1.82 [s, 6H, (CH3)2C=], 4.28 (d, 2H, CH2C=N), 7.49 and 7.75 (d, 2H, furanyl-H), 8.66 (t, 1H, NHCO), 11.72 (s, 1H, C=NOH).

Provenance & Evidence