Imidazole → 1H-Imidazol-1-ylphenylmethanone

HRID 643175

Reaction equation

HRID 643175 reaction equation
C1C=CC([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([N:20]3[CH:24]=[N:23][CH:22]=[CH:21]3)C3C=CC=CC=3)=[CH:11][CH:12]=2)=CC=1.N1C=CN=C1.C1(C(Cl)=[O:37])C=CC=CC=1>>[C:13]([N:20]1[CH:21]=[CH:22][N:23]=[CH:24]1)(=[O:37])[C:10]1[CH:9]=[CH:8][CH:7]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 795ImidazoleHCID 2378BifonazoleHCID 7412Benzoyl chloride

Product 1

HCID 663191H-Imidazol-1-ylphenylmethanoneYield 74.7%

Procedure

Bifonazole has also been prepared by benzoylation of imidazole with PhCOCl, yielding 74.7% of 1-benzoylimidazole which is subject to react with Gringnard's reactant 4-PhC6H4MgBr followed by a tosylation and subsequent reduction with sodium cyanoborohydride in hexamethylphosphoramide, to yield 68.2% Bifonazole (Es. Patent 539,345).

Sources & evidence

ORD record
ord-033c1b9274df4ed89ae8b57cb0b84483
Source dataset
uspto-grants-2010_04
Patent number
USRE041254E1

Linked notes

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