Butanedione → 4-Isopropoxymethyl-2-(p-methoxyphenyl)-5-methylimidazole hydrochloride
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
Product 1
Reagents, catalysts & solvents 1
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.).