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

HRID 1075970Notes

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-a72756c870e04875932f2d468ce98da2
Source dataset: uspto-grants-1976_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03954789

Reaction notes

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