Hydrochloric Acid → Dimethyl 2-methoxymethylimidazole-4,5-dicarboxylate

HRID 265188Notes

Reaction equation

HRID 265188 reaction equation
Cl.C([N:9]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([C:18]([O:20][CH3:21])=[O:19])[N:11]=[C:10]1[CH2:22][O:23][CH3:24])C1C=CC=CC=1>O1CCOCC1.CO.[Pd]>[CH3:24][O:23][CH2:22][C:10]1[NH:11][C:12]([C:18]([O:20][CH3:21])=[O:19])=[C:13]([C:14]([O:16][CH3:17])=[O:15])[N:9]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 19036094Dimethyl 1-benzyl-2-methoxymethylimidazole-4,5-dicarboxylate

Product 1

HCID 19036103Dimethyl 2-methoxymethylimidazole-4,5-dicarboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

650 mg of 10% w/w palladium-on-carbon and 6.1 ml of a 4N solution of hydrogen chloride in dioxane were added to a solution of 6.5 g of dimethyl 1-benzyl-2-methoxymethylimidazole-4,5-dicarboxylate [prepared as described in step (iii) above] in 65 ml of methanol. The mixture was then stirred at room temperature for 1.5 hours under a hydrogen atmosphere. At the end of this time, the catalyst was filtered off and the filtrate was concentrated by evaporation under reduced pressure, to give a crystalline compound. This crystalline compound was washed with ethyl acetate, no give 5.13 g of the hydrochloride of the title compound, melting at 108°-111° C.

Workup

  1. filtrationAt the end of this time, the catalyst was filtered off
  2. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  3. customto give a crystalline compound
  4. washThis crystalline compound was washed with ethyl acetate

Sources & evidence

ORD record
ord-6336c15a3fef44cd9099ce8627a8d024
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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