1-Methylimidazole → HCID 69040264, compound

HRID 1869617Notes

Reaction equation

HRID 1869617 reaction equation
[CH2:1]([O:5][P:6]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])([O:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:7])[CH2:2][CH2:3][CH3:4].[CH3:18][N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1>>[CH2:9]([O:8][P:6]([O-:13])([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:7])[CH2:10][CH2:11][CH3:12].[CH3:18][N+:19]1([CH2:14][CH2:15][CH2:16][CH3:17])[CH:23]=[CH:22][N:21]=[CH:20]1

Participants

3

Reactant 2

HCID 13901-MethylimidazoleHCID 31357Tributyl Phosphate

Product 1

HCID 69040264HCID 69040264, compoundYield 98.3%

Procedure

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−].

Workup

  1. stirringThe liquid was stirred at the same temperature for an additional 5 hours
  2. temperatureThe liquid was cooled
  3. custommoved to a rotary evaporator
  4. customdried at 150° C./5 mm Hg for 4 hours

Sources & evidence

ORD record
ord-2a634375f9704b8780ed0dc778dac0f6
Source dataset
uspto-grants-2009_12
Patent number
US07638636B2

Reaction notes

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