1-Methylimidazole → ethyl 1-methyl-1H-imidazole-2-carboxylate

HRID 908136Notes

Reaction equation

HRID 908136 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.C(#N)C.Cl[C:11]([O:13][CH2:14][CH3:15])=[O:12]>C(N(CC)CC)C>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 13901-MethylimidazoleHCID 6342AcetonitrileHCID 10928Ethyl chloroformate

Product 1

HCID 4261883ethyl 1-methyl-1H-imidazole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of N-methylimidazole (5 g, 0.06 mol), acetonitrile (32 mL) and triethylamine (15 mL), cooled to −20° C. was added ethyl chloroformate (13 mL, 0.137 mol), and the mixture allowed to slowly warm to room temperature and stirred for 3.5 hr. The solution was filtered (triethylamine hydrochloride) and concentrated under vacuum. The residue was purified by distillation under reduced pressure (0 Torr, 102° C.) to yield the product as a white solid. Yield (6.26 g, 68%) 1H NMR (DMSO): δ 7.44 (d, 1H, J=2.8 Hz), 7.04 (d, 1H, J=2.8 Hz), 4.26 (q, 2H, J=3.5 Hz), 3.91 (s, 3H), 1.26 (t, 3 h, J=3.5 Hz). 13C (DMSO): 159.3, 129.1, 127.7, 61.0, 36.0, 14.5.

Workup

  1. filtrationThe solution was filtered (triethylamine hydrochloride)
  2. concentrationconcentrated under vacuum
  3. distillationThe residue was purified by distillation under reduced pressure (0 Torr, 102° C.)

Sources & evidence

ORD record
ord-9f7618c45f704826b6686dfd2c837ffc
Source dataset
uspto-grants-2011_09
Patent number
US08017599B2

Reaction notes

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