2-Chloro-3-nitrothiophene → 4-Methyl-1-(3-nitrothiophen-2-yl)-1H-imidazole

HRID 1519988Notes

Reaction equation

HRID 1519988 reaction equation
Cl[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[N+:7]([O-:9])=[O:8].[CH3:10][C:11]1[N:12]=[CH:13][NH:14][CH:15]=1>>[CH3:10][C:11]1[N:12]=[CH:13][N:14]([C:2]2[S:3][CH:4]=[CH:5][C:6]=2[N+:7]([O-:9])=[O:8])[CH:15]=1

Participants

3

Reactant 2

HCID 2201862-Chloro-3-nitrothiopheneHCID 178418800HCID 178418800, compound

Product 1

HCID 687856364-Methyl-1-(3-nitrothiophen-2-yl)-1H-imidazoleYield 49%

Procedure

4-methyl-1-(3-nitrothiophen-2-yl)-1H-imidazole was prepared from 2-chloro-3-nitrothiophene and 4-methyl-1H-imidazole according to the procedure described in Example 9.7.1., above. Purification by flash column chromatography (silica, 40:60 ethyl acetate/hexane) gave the nitro intermediate (1.26 g, 49%). 1H-NMR (CDCl3) δ 7.67 (s, 1H), 7.59 (d, J=6.1 Hz, 1H), 7.19 (d, J=6.1 Hz, 1H), 6.89 (s, 1H), 2.27 (s, 3H).

Workup

  1. customPurification by flash column chromatography (silica, 40:60 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-77b3ba476596461bb6ced0b5d5fdce83
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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