Hydrochloric Acid → 4-Methylimidazol-5-ylmethanolhydrochloride

HRID 1578322Notes

Reaction equation

HRID 1578322 reaction equation
[Na+].[CH3:2][C:3]1[NH:7][CH:6]=[N:5][C:4]=1[C:8]([O-])=[O:9].C=O.O1CCOCC1.[ClH:19]>C(O)C>[ClH:19].[OH:9][CH2:8][C:4]1[N:5]=[CH:6][NH:7][C:3]=1[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 312751,4-DioxaneHCID 70578319HCID 70578319, compound

Product 1

HCID 30847074-Methylimidazol-5-ylmethanolhydrochlorideYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.48 g (0.01 mol) of 5-methylimidazole-4-carboxylic acid sodium salt, 2 ml of ~37% formaldehyde solution and 3 ml of 1,4-dioxane was heated at 75°-85° C. for 3 hours. After completion of the reaction, the solvent was stripped off, and the remaining residue was extracted with isopropanol. The isopropanol extract was concentrated to give a viscous oil. This viscous oil was dissolved in absolute ethanol and dry hydrogen chloride gas was passed through the resulting solution to afford 0.93 g of 4-hydroxymethyl-5-methylimidazole hydrochloride, m.p. 241°-244° C. Yield 63%.

Workup

  1. temperaturewas heated at 75°-85° C. for 3 hours
  2. customAfter completion of the reaction
  3. extractionthe remaining residue was extracted with isopropanol
  4. extractionThe isopropanol extract
  5. concentrationwas concentrated
  6. customto give a viscous oil

Sources & evidence

ORD record
ord-5c15087291da44919ec40e04c9766ee2
Source dataset
uspto-grants-1981_09
Patent number
US04292431

Reaction notes

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