Potassium Hydroxide → 1-(2-methoxy-4-nitrophenyl)-4-methyl-1H-imidazole

HRID 1942868Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].[CH3:13][C:14]1[N:15]=[CH:16][NH:17][CH:18]=1.[OH-].[K+]>CS(C)=O>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:17]1[CH:18]=[C:14]([CH3:13])[N:15]=[CH:16]1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 2-chloro-5-nitroanisole (187 mg, 1 mmol), of 4-methyl-1H-imidazole (335 mg, 4 mmol) and of potassium hydroxide (99 mg, 1.5 mmol) in DMSO (0.86 mL) was stirred for 5 h at 80° C. under an atmosphere of nitrogen. After cooling to 20° C. the reaction was poured onto ice-water. A precipitation was formed and the suspension was stirred for 15 min. The solid was filtered off, washed with water, dissolved in dichloromethane, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure to yield a yellow solid. The crude product was purified on silica gel using dichloromethane/methanol (19:1 v/v) as eluent to yield the title compound (106 mg, 45%) as a pale-yellow solid. Alternatively the product can be also crystallized from the crude material from diethyl ether.

Workup

additionwas poured onto ice-water
customA precipitation
customwas formed
filtrationThe solid was filtered off
washwashed with water
dissolutiondissolved in dichloromethane
dry with materialdried over sodium sulfate
filtrationfiltered
customthe solvent was evaporated under reduced pressure
customto yield a yellow solid
customThe crude product was purified on silica gel

Sources & evidence

ORD record: ord-87762245c478431a870ff8ff163f4a89
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389717B2

Reaction notes

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