Triethylamine → 1-(Methoxymethyl)-1H-imidazole-2-carboxylic acid

HRID 261949

Reaction equation

HRID 261949 reaction equation
Cl[C:2]([O:4]CC)=[O:3].[CH3:7][O:8][CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:7][O:8][CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[C:2]([OH:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 883591-(methoxymethyl)-1H-imidazole

Product 1

HCID 219727271-(Methoxymethyl)-1H-imidazole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

At a temperature of -10° C., 27.5 g. (0.25 mol) of ethyl chloroformate was added drop-wise to a solution of 28 g. (0.25 mol) of 1-(methoxymethyl)imidazole and 25 g. (0.25 mol) of triethylamine in 125 ml. of anhydrous chloroform. The mixture was stirred at 0° C. and then kept standing for two days at room temperature. The precipitated triethylamine hydrochloride was filtered off and washed with diethyl ether. The filtrate was concentrated by evaporating the solvents and the residue was dissolved in diethyl ether. The solution was dried over sodium sulphate, the ether was distilled off and the residue was distilled. The ethyl ester of 1-(methoxymethyl)imidazole-2-carboxylic acid was obtained. Boiling point 120°-124°/2 mm. Hg.

Workup

  1. customAt a temperature of -10° C., 27.5 g
  2. filtrationThe precipitated triethylamine hydrochloride was filtered off
  3. washwashed with diethyl ether
  4. concentrationThe filtrate was concentrated
  5. customby evaporating the solvents
  6. dissolutionthe residue was dissolved in diethyl ether
  7. dry with materialThe solution was dried over sodium sulphate
  8. distillationthe ether was distilled off
  9. distillationthe residue was distilled

Sources & evidence

ORD record
ord-e60a0c7e7e694c77a827280a22a9cff3
Source dataset
uspto-grants-1979_05
Patent number
US04152441

Linked notes

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