Sodium hydride → N-[2,6-Bis(1-methylethyl)phenyl]-N'-(tetradecylsulfonyl)urea

Beteiligte Stoffe

Reaktionsschritte

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.

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