Sodium Iodide → N'-(2,4-difluorophenyl)-N-heptyl-N-[5-(6-nitro-1H-benzimidazol-2-ylthio)pentyl]urea

Beteiligte Stoffe

Reaktionsschritte

Part E. To a suspension of sodium hydride (0.04 g, 60% mineral oil dispersion, 0.001 mol; washed free of mineral oil with hexane) and sodium iodide (0.15 g; 0.0011 mol) in N,N-dimethylformamide (10 mL) under a nitrogen atmosphere, cooled to 0°, a solution of 6-nitrobenzimidazol-2-thione (0.975 g; 0.005 mol) in N,N-dimethylformamide (5 mL) was added slowly. The reaction mixture was stirred for 30 minutes and then a solution of N-(5-bromopentyl)-N'-(2,4-difluorophenyl)-N-heptylurea (0.42 g, 0.001 mol) in N,N-dimethylformamide (5 mL) was added. The reaction mixture was stirred for 1 hour and then allowed to warm to ambient temperature and stirred an additional 24 hours. The reaction mixture was poured into water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with water and brine, then dried over magnesium sulfate and concentrated to give a viscous oil. The product was purified by flash chromatography on silica gel eluting with hexane:ethyl acetate (75:25::v:v) to give the title compound (1.2 g, 0.00337 mol) as a solid, mp 120°-122°. 1H NMR (DMSO-d6) δ13.25 (bs,1H), 8.27 (bs,1H), 8.05 (d,1H,J=7.6 Hz), 7.91 (s,1H), 7.57 (d,1H,J=7.6 Hz), 7.4-7.3 (m,1H), 7.25-7.12 (m,1H), 7.0-6.8 (m,1H), 3.37-3.16 (m,6H), 1.85-1.72 (m,2H), 1.6-1.35 (m,6H), 1.27-1.1 (m,8H), 0.83 (t,3H,J=6.8 Hz).

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