反应详情

A solution of 1-tetradecylsulfonamide (9.0 g, 32.4 mmoles) in DMF (90 mL) was added dropwise to a stirred suspension of NaH (1.63 g, 68 mmoles) in 30 mL of DMF. The solution was stirred 60 minutes, then 2,6-diisopropylphenyl isocyanate (7.0 mL, 33 mmoles) was added dropwise. The mixture was stirred overnight at room temperature, then quenched by dropwise addition of 1M HCl. The mixture was then partitioned between H2O and ethyl acetate (500 mL each). The aqueous layer was further extracted with ethyl acetate. The combined ethyl acetate extracts were diluted with hexane (100 mL) and then washed exhaustively with H2O. The organic extracts were dried, filtered, and concentrated to a solid residue, which was triturated with ether and the solid isolated by suction filtration and dried. Isolated 9.70 g of solid, m.p. 135°-137° C.

1. stirringThe mixture was stirred overnight at room temperature
2. customquenched by dropwise addition of 1M HCl
3. customThe mixture was then partitioned between H2O and ethyl acetate (500 mL each)
4. extractionThe aqueous layer was further extracted with ethyl acetate
5. additionThe combined ethyl acetate extracts were diluted with hexane (100 mL)
6. washwashed exhaustively with H2O
7. customThe organic extracts were dried
8. filtrationfiltered
9. concentrationconcentrated to a solid residue, which
10. customwas triturated with ether
11. customthe solid isolated by suction filtration
12. customdried