Bis-(1H-imidazol-2-YL)-methanone → HCID 44254680, compound

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Reaction Steps

To 2,6-difluoroaniline (8 g, 62 mmol) in dimethylformamide (100 mL) was added a 2 M solution in tetrahydrofuran of ethyl amine (93 mL, 186 mmol) and the reaction stirred at room temperature overnight. The reaction was partitioned between 1 N hydrochloric acid and ethyl acetate and dried over sodium sulfate. The product was purified by silica gel using the ISCO (0-100% ethyl acetate/hexane) to give an equal mixture of ethyl-(3-fluoro-2-nitro-phenyl)-amine and N,N′-Diethyl-2-nitro-benzene-1,3-diamine. This mixture was reduced using the parr shaker and a spatula tip of 5% Pd/C in MeOH (100 mL). Upon complete reduction, the reaction was filtered through a pad of celite and concentrated onto silica gel. The desired product was purified on silica gel using the ISCO (0-100% ethyl acetate/hexane) to give N1-Ethyl-3-fluoro-benzene-1,2-diamine (2.48 g, 52%). N1-Ethyl-3-fluoro-benzene-1,2-diamine (2.48 g, 16.1 mmol) and carbonyl diimidazole (4.38 g, 27 mmol) in tetrahydrofuran (50 mL) was stirred at room temperature overnight. Upon disappearance of the starting material, the reaction was partitioned between 1 N hydrochloric acid (100 mL) and ethyl acetate (100 mL). The organics were dried over sodium sulfate and concentrated to give 1-ethyl-4-fluoro-1,3-dihydro-2H-benzimidazol-2-one as a white solid in near quantitative yield. MS (ES) m/z 181.1;

Provenance & Evidence