Methyl chloroacetate → 1,3-Bis(2-methoxy-2-oxoethyl)-1H-imidazol-3-ium chloride

HRID 76773

Reaction equation

[Cl:1][CH2:2][C:3]([O:5][CH3:6])=[O:4].C[Si](C)(C)[N:9]1[CH:13]=[CH:12][N:11]=[CH:10]1>>[Cl-:1].[CH3:6][O:5][C:3](=[O:4])[CH2:2][N:11]1[CH:12]=[CH:13][N+:9]([CH2:2][C:3](=[O:4])[O:5][CH3:6])=[CH:10]1

Participants

Reactant 2

HCID 7295Methyl chloroacetate

HCID 28925(Trimethylsilyl)imidazole

Product 1

HCID 867627401,3-Bis(2-methoxy-2-oxoethyl)-1H-imidazol-3-ium chlorideYield 99.7%

Conditions

Temperature: 60 °C

Procedure

Methyl chloroacetate (2; 29.8 mL, 338.6 mmol, 2.0 eq) was added drop-wise to 1-(trimethylsilyl)-1H-imidazole (8; 25.0 mL, 169.3 mmol). The mixture was heated at 60° C. for 24 hours. The mixture was cooled to room temperature, washed with Et2O (3×500 mL) and dried in vacuo yielding 9 (41.97 g, 168.8 mmol, 99.7%) as a white solid.

Workup

temperatureThe mixture was cooled to room temperature
washwashed with Et2O (3×500 mL)
customdried in vacuo

Sources & evidence

ORD record: ord-f0327e03632d45c29e19be139b70e8eb
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835650B1

Linked notes

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