Water → HCID 22449363, compound

A solution of malononitrile (4.0 g, 60 mmol) in tetrahydrofuran (25 ml), was added dropwise over an hour to an ice-cooled suspension of sodium hydride (4.80 g, 60%, 120 mmol) in tetrahydrofuran (75 ml), and the mixture stirred at room temperature for an hour, and then re-cooled to 0° C. A solution of phenylacetyl chloride (8.0 ml, 60 mmol) in tetrahydrofuran (20 ml) was added dropwise over an hour, maintaining the temperature below 10° C., and the reaction mixture then stirred at room temperature for 36 hours. Water (10 ml) was added, the mixture concentrated under reduced pressure, the residue partitioned between ether (50 ml), and 1N hydrochloric acid (50 ml) and the phases separated. The aqueous layer was extracted with ether (2×50 ml), the combined organic layers washed with brine (50 ml), dried (Na2SO4) and evaporated under reduced pressure. The residue was dissolved in acetonitrile (100 ml), filtered to remove residual silicon oil, and the filtrate evaporated under reduced pressure, to afford the title compound as a brown oil, (11.20 g).

1. temperaturecooled
2. temperaturere-cooled to 0° C
3. temperaturemaintaining the temperature below 10° C.
4. stirringthe reaction mixture then stirred at room temperature for 36 hours
5. concentrationthe mixture concentrated under reduced pressure
6. customthe residue partitioned between ether (50 ml), and 1N hydrochloric acid (50 ml)
7. customthe phases separated
8. extractionThe aqueous layer was extracted with ether (2×50 ml)
9. washthe combined organic layers washed with brine (50 ml)
10. dry with materialdried (Na2SO4)
11. customevaporated under reduced pressure
12. dissolutionThe residue was dissolved in acetonitrile (100 ml)
13. filtrationfiltered
14. customto remove residual silicon oil
15. customthe filtrate evaporated under reduced pressure

ORD record

ord-f2e0c22f66fb41f7a06da9477d96363a

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06407114B1