4-Methoxybenzenecarboximidamide → 2-(4-Methoxyphenyl)-4-(2-nitrophenyl)imidazole

HRID 378899

Reaction equation

Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12])=O.[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH2:22])=[NH:21])=[CH:18][CH:17]=1>C(#N)C>[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]2[NH:22][CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N+:11]([O-:13])=[O:12])[N:21]=2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 2-bromo-2′-nitroacetophenone (18 g), 4-methoxybenzamidine (20 g), and silica gel (20 g) in acetonitrile (500 ml) is heated at 40° C. for 24 hours. The reaction is evaporated and the residue put on a layer of silica gel and eluted with 50% ethyl acetate/hexane (1500 ml). The solution is evaporated under reduced pressure to approximately 250 ml and extracted with 5% HCl (3×250 ml). The combined aqueous solution is basified with K2CO3 and extracted with ethyl acetate (3×400 ml) to afford 2-(4-methoxyphenyl)-4-(2-nitrophenyl)-imidazole (17 g) as a dark yellow oil which is used in the next step without further purification.

Workup

customThe reaction is evaporated
washthe residue put on a layer of silica gel and eluted with 50% ethyl acetate/hexane (1500 ml)
customThe solution is evaporated under reduced pressure to approximately 250 ml
extractionextracted with 5% HCl (3×250 ml)
extractionextracted with ethyl acetate (3×400 ml)

Sources & evidence

ORD record: ord-ad59b6e86cc441af88a72d2c9740d441
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06297252B1

Linked notes

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