Sodium hydride → HCID 44315917, Verbindung

A solution of 2-pentadecylsulfonamide (2.91 g, 10 mmoles) in DMF (40 mL dried over 3 Å sieves) was added dropwise to a stirred, 0° C. suspension of NaH (0.5 g, 21 mmoles of hexane washed) in 10 mL dry DMF. The mixture was stirred 30 minutes at 0° C., then warmed to room temperature for 3 hours. It was then cooled back to 0° C. and a solution of 2,6-diisopropylphenylisocyanate (2.14 mL, 10 mmoles) in 10 mL DMF was added dropwise. The mixture was allowed to warm to room temperature overnight, cooled to 0° C., and quenched by dropwise addition of 1N HCl (60 mL). The mixture was partitioned between EtOAc (300 mL) and H2O (100 mL). The organic layer was further washed with brine, dried, filtered, and evaporated to provide an oil which was flash chromatographed (silica gel, 4:1 hexane-EtOAc) to produce 3 g of an oil which solidified on standing (m.p. 65°-75° C.).

1. temperaturewarmed to room temperature for 3 hours
2. temperatureIt was then cooled back to 0° C.
3. temperatureto warm to room temperature overnight
4. temperaturecooled to 0° C.
5. customquenched by dropwise addition of 1N HCl (60 mL)
6. customThe mixture was partitioned between EtOAc (300 mL) and H2O (100 mL)
7. washThe organic layer was further washed with brine
8. customdried
9. filtrationfiltered
10. customevaporated
11. customto provide an oil which
12. customchromatographed (silica gel, 4:1 hexane-EtOAc)

ORD-Eintrag

ord-35a33621d7b64952b24bea5877322456

Quelldatensatz

uspto-grants-1993_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05254589