1-Methylimidazole → HCID 69040264, compound

Participants

Reaction Steps

Tributylphosphate (137.2 g, 0.505 mole) was added dropwise, slowly, to a 300 ml flask containing 41.5 g (99%, 0.5 mole) N-methylimidazole at 170° C. under nitrogen and stirring. The liquid was stirred at the same temperature for an additional 5 hours. The liquid was cooled and moved to a rotary evaporator and dried at 150° C./5 mm Hg for 4 hours. The product (171.3 g, yield 98%) was pure, as judged from NMR, and was liquid at room temperature. 1H-NMR (CDCl3, 300.13 MHz, δ): 10.37 (s, 1H, —N—CH═N—), 7.50 (s, 1H, —N—CH═CH—N—), 7.29)s, 1H, —N—CH═CH—N—), 4.09 (t, 2H, —N—CH2—CH2CH2CH3), 3.87 (s, 3H, —N—CH3), 3.67 (m, 4H, —O—CH2—CH2CH2CH3), 1.67 (qu, 2H, —NCH2—CH2—CH2CH3), 1.40 (m, 4H, 2×—OCH2—CH2—CH2CH3), 1.16 (m, 4H, —OCH2CH2—CH2—CH3), 1.16 (m, 2H, —NCH2CH2—CH2CH3), 0.70 (m, 6H, 2×—OCH2CH2CH2—CH3), 0.70 (m, 3H, —NCH2CH2CH2—CH3). 31P-NMR (CDCl3, 81.015 MHz, δ): 0.95 [s, (RO)2—P(═O)—O−].

Provenance & Evidence