Sodium hydride → HCID 178503673, compound

Temperature

60 °C

To a solution of N-sulfamyl-3-(methylthio)propionamidine (4.9 gm, 25 mmol) in dry tetrahydrofuran (75 ml) under nitrogen there was added 60% sodium hydride in mineral oil (1.0 gm, 25 mmol). This mixture was warmed at 60° C. for 1/2 hour as a copious precipitate formed. To this suspension, a solution of phenylcyanate (3.0 gm, 25 mmol) in dry THF was added dropwise giving a homogeneous solution. After 1/2 hour, additional 60% sodium hydride in mineral oil (1.0 gm, 25 mmol) was added and the resultant solution warmed at 50° C. for 20 hours. The reaction mixture was diluted with diethyl ether and the precipitate collected by filtration. This precipitate was dissolved in water, acidified with dilute HCl, filtered and the aqueous solution extracted with 3% methanol/chloroform and then the water removed under vacuum. The residue was extracted with acetonitrile, filtered, and the extract evaporated to give crude product (2.0 gm). This material was chromatographed on silica gel and eluted with 5- 10% methanol/chloroform. Upon concentration of the appropriate fractions, the product crystallized, (1.4 gm), m.p. 243°-246° C.

1. customformed
2. customgiving a homogeneous solution
3. filtrationthe precipitate collected by filtration
4. dissolutionThis precipitate was dissolved in water
5. filtrationfiltered
6. extractionthe aqueous solution extracted with 3% methanol/chloroform
7. customthe water removed under vacuum
8. extractionThe residue was extracted with acetonitrile
9. filtrationfiltered
10. customthe extract evaporated

ORD record

ord-c22a896492514b40af2b0299107c0980

Source dataset

uspto-grants-1985_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04497810