Diazomethane → Ethanone, 1-(1-methyl-2-nitro-1H-imidazol-5-yl)-

HRID 1288034Notes

Reaction equation

[CH3:1][N:2]1[C:6]([CH:7]=[O:8])=[CH:5][N:4]=[C:3]1[N+:9]([O-:11])=[O:10].[N+](=[CH2:14])=[N-]>C(OCC)C>[C:7]([C:6]1[N:2]([CH3:1])[C:3]([N+:9]([O-:11])=[O:10])=[N:4][CH:5]=1)(=[O:8])[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 0.70 g. of 1-methyl-2-nitro-5-imidazolecarboxaldehyde in 180 ml. of diethyl ether, a solution of 0.43 g. of diazomethane in 86 ml. of diethyl ether is added under cooling at about 0° C. After standing at room temperature for 7 days, the reaction mixture is filtered and then evaporated to dryness. The residue (0.60 g.), dissolved in 6 ml. of chloroform, is chromatographed on 6 plates of silica gel, eluting with a 9:1 (v/v) chloroform:methanol mixture, and TLC spots are visualized under U.V. light. The silica gel, which corresponds to an Rf value from 0.64 up to 0.76 is collected and extracted with methanol. From this solution, after filtration and concentration, 0.065 g. of 5-acetyl-1-methyl-2-nitroimidazole is obtained, m.p. 81°-83° C.

Workup

filtrationthe reaction mixture is filtered
customevaporated to dryness
dissolutionThe residue (0.60 g.), dissolved in 6 ml
customof chloroform, is chromatographed on 6 plates of silica gel
washeluting with a 9:1 (v/v) chloroform
customis collected
extractionextracted with methanol
filtrationFrom this solution, after filtration and concentration, 0.065 g

Sources & evidence

ORD record: ord-a4f7ac1c3c874bf5af5acee388297dd0
Source dataset: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03987053

Reaction notes

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