Potassium Hydroxide → 1-(2-(allyloxy)-4-nitrophenyl)-4-chloro-1H-imidazole

HRID 474226Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[CH2:7]([O:10][C:11]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:12]=1Cl)[CH:8]=[CH2:9].[OH-].[K+]>CS(C)=O>[CH2:7]([O:10][C:11]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:12]=1[N:5]1[CH:6]=[C:2]([Cl:1])[N:3]=[CH:4]1)[CH:8]=[CH2:9]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-chloro-1H-imidazole (3.31 g, 32.0 mmol), 2-(allyloxy)-1-chloro-4-nitrobenzene (6.50 g, 30.8 mmol), and potassium hydroxide flakes (1.90 g, 33.9 mmol) in anhydrous DMSO (50 mL) was heated at 90° C. for 20 h under nitrogen. The reaction mixture was allowed to cool to rt and ice-cold water was added. The resulting precipitate was collected by vacuum filtration. The product was dried, and purified by column chromatography (5% EtOAc/Hexane) to afford the yellow solid 1-(2-(allyloxy)-4-nitrophenyl)-4-chloro-1H-imidazole (3.48 g, 40% yield). LC-MS (M+H)+280.2. 1H NMR (400 MHz, CDCl3) δ ppm 7.97-7.93 (2H, m), 7.77 (1H, s), 7.44 (1H, d, J=8.8 Hz), 6.05-5.98 (1H, m), 5.45-5.37 (2H, m), 4.70-4.65 (2H, m).

Workup

temperatureto cool to rt
additionice-cold water was added
filtrationThe resulting precipitate was collected by vacuum filtration
customThe product was dried
custompurified by column chromatography (5% EtOAc/Hexane)

Sources & evidence

ORD record: ord-bb48a969e3024c29a62d237734d4fd43
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637523B2

Reaction notes

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