Hydrogen Peroxide → HCID 19419822, compound

Temperature

0 °C

A mixture containing 20 g of 93 percent purity (99 mmol) 4-chloro-2-ethoxy-6-hydrazinopyrimidine in a solvent composed of 90 mL of acetonitrile and 26 mL of water was prepared under nitrogen in a 500 mL flask equipped with a condensor and an opening covered by a septum through which the syringe of a syringe pump was inserted. To this was added 11.3 g (148 mmol) of carbon disulfide and, after a 15-min reaction period, 16.7 g of 30 percent aqueous hydrogen peroxide (147 mmol) was added over a 15-min period by means of the syringe with stirring and cooling to hold the temperature at about 25° C. The mixture was allowed to react for another 4 hours and then was cooled to about 0° C. The precipitated product and sulfur by-product were recovered by vacuum filtration and washed with water, a 1:1 mixture of water and acetonitrile, and finally acetonitrile. The wet cake was slurried in 1 L of water at 70° C. and about 600 mL of acetonitrile was added to dissolve the solid. The resulting mixture was gravity filtered and the filtrate was allowed to cool over the weekend. The mixture was further cooled in a refrigerator and the crystals that formed were recovered by vacuum filtration, washed with acetonitrile, and dried to constant weight to obtain 14.1 g (62 percent of theory) of the title compound as an amber solid which decomposed on heating above 187° C.

1. customwas prepared under nitrogen in a 500 mL flask
2. customequipped with a condensor
3. additionwas added over a 15-min period by means of the syringe
4. temperaturecooling
5. customat about 25° C
6. customto react for another 4 hours
7. filtrationThe precipitated product and sulfur by-product were recovered by vacuum filtration
8. washwashed with water
9. additiona 1:1 mixture of water and acetonitrile, and finally acetonitrile
10. customwas slurried in 1 L of water at 70° C.
11. additionabout 600 mL of acetonitrile was added
12. dissolutionto dissolve the solid
13. filtrationfiltered
14. temperatureto cool over the weekend
15. temperatureThe mixture was further cooled in a refrigerator
16. customthe crystals that formed
17. filtrationwere recovered by vacuum filtration
18. washwashed with acetonitrile
19. customdried to constant weight

ORD record

ord-917162d2221c4a24b0bb1f08d04e21c7

Source dataset

uspto-grants-1996_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05563269