1,1'-Carbonyldiimidazole → Tert-butyl 2-[(4-aminobenzyl)carbamoyl]hydrazinecarboxylate

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Reaction Steps

To a suspension of 1,1′-carbonyldiimidazole (1.783 g, 11.00 mmol) in anhydrous tetrahydrofuran (7 ml) was added tert-butyl carbazate (1.322 g, 10.00 mmol), and the mixture was stirred at room temperature for 30 min. A solution of 4-(aminomethyl)aniline (1.228 g, 10.05 mmol) in anhydrous tetrahydrofuran (3 ml) was added, and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under to reduced pressure, and ethyl acetate (50 ml) and water (50 ml) were added to the residue. The mixture was stirred, stood still and partitioned. The aqueous layer was extracted twice with ethyl acetate, and the combined organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 90 g, ethyl acetate:hexane=7:3→8:2→9:1) to give tert-butyl 2-[(4-aminobenzyl)carbamoyl]hydrazinecarboxylate (2.180 g, 7.778 mmol, yield 77.8%) as a white solid.

Provenance & Evidence