Hydrochloric Acid → (5-Amino-1,2,4-thiadiazol-3-yl)[(fluoromethoxy)imino]acetic acid

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyl 2-fluoromethoxyimino-2-(5-formamido-1,2,4-thiadiazole-3-yl)-acetate (syn-isomer) (5.24 g, 20 mmol) in water (26 ml), sodium hydroxide (3.2 g, 80 mmol) in water (16 ml) was added at 0° C., and the mixture was stirred at 5° C. for 30 hrs. and then adjusted to pH 1 or lower with concentrated hydrochloric acid (7.0 ml, 84 mmol), and extracted four times with ethyl acetate (30 ml). The resulting ethyl acetate layer was dried over sodium sulfate and decolorized with activated carbon (0.5 g). The ethyl acetate was distilled off, to the residue, isopropyl ether was added. The resultant solution was cooled to precipitate. The precipitates were filtered off and dried to give 2-fluoromethoxyimino-2-(5-amino-1,2,4-thiadiazole-3-yl) acetic acid (syn-isomer) (36 g, yield: 81.8%).

Provenance & Evidence