1-Methylimidazole → HCID 69043066, compound

HRID 1869616Notes

Reaction equation

[CH3:1][O:2][P:3]([O:7]C)([O:5][CH3:6])=[O:4].[CH3:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1>>[CH3:1][O:2][P:3]([O-:7])([O:5][CH3:6])=[O:4].[CH3:9][N+:10]1([CH3:1])[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

Reactant 2

HCID 13901-Methylimidazole

HCID 10541Trimethyl Phosphate

Product 1

HCID 69043066HCID 69043066, compoundYield 197.8%

Conditions

Temperature: 140 °C

Procedure

Trimethylphosphate (127.6 g, 0.883 mole) was added dropwise over a period of 1 hour to a 300 ml flask containing 72.2 g (99%, 0.87 mole) N-methylimidazole at room temperature. The temperature of the reaction mixture was slowly increased to 140° C. As the reaction mixture approached 140° C., there was an acceleration in the rate at which the temperature increased. The reaction mixture was stirred at the same temperature for an additional 3 hours. The mixture was cooled and moved to a rotary evaporator and dried at 150° C./5 mm Hg for 4 hours. The product (194 g, yield 100%) was pure, judged from NMR and liquid at room temperature. 1H-NMR (CDCl3, 300.13 MHz, δ): 10.40 (s, 1H, —N—CH═N—), 7.43 (s, 2H, —N—CH═CH—N—), 3.91 (s, 6H, N—CH3), 3.46 (d, 6H, —OCH3). 31P-NMR (CDCl3, 81.015 MHz, δ): 3.01 [s, (RO)2—P(═O)—O−].

Workup

customapproached 140° C.
temperatureincreased
temperatureThe mixture was cooled
custommoved to a rotary evaporator
customdried at 150° C./5 mm Hg for 4 hours

Sources & evidence

ORD record: ord-0875677fc4ce41daaa71305329395c19
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07638636B2

Reaction notes

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