Diethyl Ether → 2-(2-(Methylamino)-1H-benzo[d]imidazol-1-yl)ethan-1-ol

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

According to the procedure of B. Agai, et al., Tetrahedron, 32, 839, (1976), to a cooled (0° C.), stirred suspension of 2-(2-aminoanilino)ethanol (30.4 g, 0.200 mol) in MeOH (100 mL) was added a solution of CH3NCS (14.6 g, 0.200 mol) in MeOH (60 mL) dropwise. The resulting mixture was stirred at room temperature for 4 hours and then heated under reflux for 15 minutes. CH3I (28.4 g, 0.200 mol) was added and the mixture was heated under reflux for 10 minutes, cooled to room temperature and stirred for 2 hours. Ether (200 mL) was added and the resulting precipitate was collected by filtration, taken up in nBuOH (140 mL), and heated under reflux for 10 hours. The mixture was cooled in the freezer for 3 hours and the white crystals were filtered. The material was dissolved in H2O and the solution was neutralized with 10% aqueous K 2 CO3. The white solid was collected by filtration to give 8.2 g (21%) of product m.p. >200° C.

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