Formamide → 5-(3-Methoxyphenyl)-1H-imidazole

HRID 747310

Reaction equation

HRID 747310 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)=O.[CH:13]([NH2:15])=O.C(Cl)Cl.CO.[NH4+:21].[OH-]>>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:3]2[NH:15][CH:13]=[N:21][CH:2]=2)[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 713FormamideHCID 101294Bromomethyl 3-methoxyphenyl ketoneHCID 21896990Dichloromethane methanol ammonium hydroxide

Product 1

HCID 220186495-(3-Methoxyphenyl)-1H-imidazoleYield 43%

Procedure

Reaction of 2-bromo-1-(3-methoxy-phenyl)-ethanone (2.5 g, 10.90 mmol), and formamide (3.1 mL, 76.40 mmol), followed by chromatography (CH2Cl2/MeOH/NH4OH 48:1:1) gave the title compound (820 mg, 43%) as a white solid. 1H NMR (300 MHz, CD3OD) δ 3.83 (s, 3H), 6.78-6.82 (m, 1H), 7.26-7.28 (m, 3H), 7.42 (s, 1H), 7.72 (s, 1H).

Sources & evidence

ORD record
ord-4af4aa12214d4224add3015d15b440bb
Source dataset
uspto-grants-2008_07
Patent number
US07396840B2

Linked notes

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