Mefenidil → Butanedione
反応式
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]参加物
実験手順
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##
出典と根拠
- ORDレコード
- ord-67d3c91f1dc940dd8d1eaf279f0cf1fe
- 出典データセット
- uspto-grants-1978_06
- 特許番号
- US04093811
反応ノート
読み込み中…