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

HRID 1519974Notes

Reaction equation

HRID 1519974 reaction equation
Cl[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[N+:7]([O-:9])=[O:8].[CH3:10][N:11]1[CH:15]=[C:14]([Sn](CCCC)(CCCC)CCCC)[N:13]=[CH:12]1>>[CH3:10][N:11]1[CH:15]=[C:14]([C:2]2[S:3][CH:4]=[CH:5][C:6]=2[N+:7]([O-:9])=[O:8])[N:13]=[CH:12]1

Participants

3

Reactant 2

HCID 2201862-Chloro-3-nitrothiopheneHCID 219011411-Methyl-4-(tributylstannyl)-1H-imidazole

Product 1

HCID 687845921-Methyl-4-(3-nitrothiophen-2-yl)-1H-imidazole

Conditions

Temperature
95 °C

Procedure

The title compound was prepared from 2-chloro-3-nitrothiophene (2.57 g, 15.7 mmol) and 1-methyl-4-(tributylstannyl)-1H-imidazole (8.64 g, 23.3 mmol) using protocol E except the reaction was heated to 90° C. (rather than 95° C.) and was purified by flash chromatography (hexane:ethyl acetate). Method [1] Retention time 0.57 min by HPLC (MH+ 210).

Workup

  1. customwas purified by flash chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-4770828d10bb4d8cabd4b8be49830a9e
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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