Mefenidil → Butanedione
Reaction equation
C(CC1[N:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:7]C=1C)#N.[CH3:16][C:17]1([OH:30])[C:21]([CH3:23])([OH:22])NC(C2C=CC=CC=2)=N1>O>[C:6]([NH2:7])(=[NH:5])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:21]([C:17]([CH3:16])=[O:30])([CH3:23])=[O:22]Participants
Reactant 2
Product 2
Reagents, catalysts & solvents 1
Procedure
An alternative method of preparing the preferred compound, 4-cyanomethyl-5-methyl-2-phenylimidazole (X), is from the precursor, 4,5-dimethyl-2-phenylimidazoline-4,5-diol (VII), preferably in the form of a mineral acid addition salt. The precursor (VII), which is described by O. Diels and K. Schleich, Ber. 49, 1711 (1916), may be obtained by the reaction of benzamidine with biacetyl in water. By heating (VII) in a strong non-oxidizing mineral acid, preferably dilute HCl, under reflux conditions (about 95° C) for about 1-2 hours, and then cooling the reaction mixture to about 0° C for maximal precipitation conditions, there is obtained 5(4)-methyl-2-phenylimidazole-4(5)-methanol (VIII), the hydroxy function of which is then transformed successively to the chloride (IX) and then to the nitrile (X), as previously described, to yield the desired 4-cyanomethyl-5-methyl-2-phenyl-imidazole. The foregoing reactions may be illustrated by the following schematic flow chart: ##STR3##
Sources & evidence
- ORD record
- ord-67d3c91f1dc940dd8d1eaf279f0cf1fe
- Source dataset
- uspto-grants-1978_06
- Patent number
- US04093811
Reaction notes
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