Methoxymethyl isocyanate → HCID 49868655, compound

Participants

Reaction Conditions

Reaction Steps

Sodium nitrite (150 mg, 2.1 mmol) in water (1 mL) was added to a suspension of (E)-4-(2-(thiophen-2-yl)vinyl)-1H-imidazol-5-amine (0.35 g, 1.8 mmol) in 10% HBF4 (4 mL) at 0° C. After stirring at 0° C. for 60 minutes, the precipitate was filtered from solution and dried over P2O5. This diazo compound (IR stretch 2193 cm−1) was used without further purification. Methoxymethyl isocyanate (0.43 g, 4.9 mmol) was added to a solution of (E)-4-diazo-5-(2-(thiophen-2-yl)vinyl)-4H-imidazole (0.3 g, 1.47 mmol) in dry DMSO (2 mL) under nitrogen. The resulting solution was stirred at room temperature for 48 hours, then purified by column chromatography (DCM) to give the title compound as a yellow solid (50 mg, 12%). δH (CDCl3) 8.44 (1H, s), 7.95 (1H, d, J=15.6), 7.34 (1H, d, J=5.1), 7.31 (1H, d, J=15.6), 7.26 (1H, d, J=3.6), 7.08 (1H, dd, J=5.1, 3.6), 5.69 (2H, s), 3.57 (3H, s).

Provenance & Evidence