Mefenidil → Butanedione

HRID 839124노트

반응식

HRID 839124 반응식
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]

참가 물질

5

반응물 2

HCID 65475MefenidilHCID 203258994,5-Dimethyl-2-phenylimidazoline-4,5-diol2회

생성물 2

HCID 650ButanedioneHCID 2332Benzamidine

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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##

출처 및 근거

ORD 기록
ord-67d3c91f1dc940dd8d1eaf279f0cf1fe
출처 데이터셋
uspto-grants-1978_06
특허 번호
US04093811

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