Dimethylformamide → (2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(fluoromethoxyimino)acetyl chloride

Temperature

-12 °C

In 30.0 ml of tetrahydrofuran (THF), 10.0 g (45.42 mmol) of 2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)fluoromethoxyiminoacetic acid were stirred at room temperature to completely dissolve the latter in the former, followed by cooling to -12° C. Added dropwise to the reaction mixture was a chlorinating reagent, which had been prepared beforehand by gradually adding 7.65 g (49.89 mmol) of phosphorus oxychloride at 5° C. into a mixture of 20 ml of THF and 3.7 g (49.93 mmol) of N,N-dimethylformamide (DMF) and then reacting them for 30 minutes. Subsequent to their reaction for 60 minutes with the temperature maintained at -15° C., the reaction mixture was poured into 150 ml of ice water and was then stirred for 20 minutes to precipitate crystals. The crystals were collected by filtration, washed twice with 15 ml aliquots of ice water and then, under reduced pressure, dried, whereby the title compound was obtained. Yield: 8.50 g (77.9%). Purity: 95.7%.

1. dissolutionto completely dissolve the latter in the former,
2. additionAdded dropwise to the reaction mixture
3. customhad been prepared beforehand
4. customfor 30 minutes
5. customSubsequent to their reaction for 60 minutes with the temperature
6. temperaturemaintained at -15° C.
7. customto precipitate crystals
8. filtrationThe crystals were collected by filtration
9. washwashed twice with 15 ml aliquots of ice water
10. customunder reduced pressure, dried

ORD record

ord-5127e02166844a59b09de99b1b1a5992

Source dataset

uspto-grants-1995_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05428173