Toluene → HCID 57437089, compound

Participants

Reaction Steps

4-Methylimidazole (6.7 g, 81.5 mmoles) and 2-(mesyloxy)-1-[2-[(tert-butoxycarbonyl)amino]phenyl]ethane (23.37 g, 74.1 mmoles) (Ref.:D. Critch and X. Hao, J. Org. Chem., 62, 1997, 5982-5988) were dissolved in anhydrous toluene (250 mL) and anhydrous dichloromethane (50 mL) and the mixture was heated under an argon atmosphere at 80° C. for 30 h. and then allowed to stand at 25° C. for 41 h. The solution was evaporated to dryness and the residue was chromatographed on silica gel using dichloromethane, then 3% (conc. NH4OH in methanol)-dichloromethane as the eluant to give N-tert-butoxyindoline (2.82 g, 22%) (Ref.: I. Masatomo and K. Tsukasa, Heterocycles, 34(5), 1992, 1031-1038) and the title mixture of imidazole compounds (4-Methyl:5-Methyl::66%:34%) (3.88 g, 34%).

Provenance & Evidence