Butanedione → 4-Isopropoxymethyl-2-(p-methoxyphenyl)-5-methylimidazole hydrochloride

HRID 839125

Reaction equation

HRID 839125 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[NH:9])=[CH:6][CH:5]=1.[C:13]([C:16]([CH3:18])=O)([CH3:15])=O>C(O)(C)C>[ClH:1].[CH:4]([O:3][CH2:15][C:13]1[N:9]=[C:8]([C:7]2[CH:11]=[CH:12][C:4]([O:3][CH3:2])=[CH:5][CH:6]=2)[NH:10][C:16]=1[CH3:18])([CH3:12])[CH3:5]

Participants

4

Reactant 2

HCID 650ButanedioneHCID 123262194-Methoxybenzamidine Hydrochloride

Product 1

HCID 203258814-Isopropoxymethyl-2-(p-methoxyphenyl)-5-methylimidazole hydrochlorideYield 161.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 38.4 g (0.206 mole) of p-methoxy-benzamidine hydrochloride in 1 liter of refluxing isopropyl alcohol is added 25 g (0.25 mole) of biacetyl. The mixture is stirred and refluxed for 72 hours. The solvent is removed to dryness under reduced pressure and the solid residue taken up in fresh hot isopropyl alcohol. Ether is added and, on chilling, pale yellow crystals form which are collected to give about 49.5 g (81% yield) of 4-isopropoxymethyl-2-(p-methoxyphenyl)-5-methylimidazole hydrochloride as very pale yellow crystals, m.p. 149°-150° C (dec.). Recrystallization twice from isopropyl alcohol-ether with charcoaling gives the product as white crystals, m.p. 149°-150° C (dec.).

Workup

  1. temperaturerefluxed for 72 hours
  2. customThe solvent is removed to dryness under reduced pressure
  3. additionEther is added
  4. temperatureon chilling
  5. custompale yellow crystals form which are collected

Sources & evidence

ORD record
ord-b69325bec56f42c09d77d025d7214a05
Source dataset
uspto-grants-1978_06
Patent number
US04093811

Linked notes

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