Cyclohexanol → 5-Cyclohexyloxy-2-carbomethoxyaminobenzimidazole

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Reaction Steps

A mixture of cyclohexanol (0.03 mol) in 75 ml. of dry dimethylformamide under nitrogen is agitated while 55% sodium hydride (0.03 mol) in oil is added portionwise. When evolution of hydrogen ceases 2-nitro-5-chloroaniline (0.025 mol) is added with stirring. The mixture is warmed at 75°-80° C. for 1 hour then poured onto 6 volumes of ice slurry. The separated product is recrystallized from water to give red crystals of the nitroaminobiphenylether. After hydrogenation and reaction with carbomethoxycyanamide as described above the product, 5-cyclohexyloxy-2-carbomethoxyaminobenzimidazole is obtained.

Provenance & Evidence