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

Temperature

5 °C

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%).

1. additionwas added at 0° C.
2. extractionextracted four times with ethyl acetate (30 ml)
3. dry with materialThe resulting ethyl acetate layer was dried over sodium sulfate
4. distillationThe ethyl acetate was distilled off, to the residue, isopropyl ether
5. additionwas added
6. temperatureThe resultant solution was cooled
7. customto precipitate
8. filtrationThe precipitates were filtered off
9. customdried

ORD record

ord-c4a0edef2ccb4728aac97e45344b987a

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05773624