N-methylhydroxylamine hydrochloride → alpha-(1-Methyl-2-nitroimidazole-5-yl)-N-methylnitrone

HRID 1288019

Reaction equation

HRID 1288019 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]=O)=[CH:5][N:4]=[C:3]1[N+:9]([O-:11])=[O:10].Cl.[CH3:13][NH:14][OH:15].C(=O)(O)[O-].[Na+]>C(O)C>[CH3:1][N:2]1[C:6]([CH:7]=[N+:14]([CH3:13])[O-:15])=[CH:5][N:4]=[C:3]1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 77906N-methylhydroxylamine hydrochlorideHCID 1003901-Methyl-2-nitro-1H-imidazole-5-carboxaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 325650alpha-(1-Methyl-2-nitroimidazole-5-yl)-N-methylnitrone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.250 g. of 1-methyl-2-nitro-5-imidazolecarboxaldehyde, 0.150 g. of N-methylhydroxylamine hydrochloride and 0.150 g. of sodium bicarbonate is refluxed in 80 ml. of anhydrous ethanol for 2 hours and after filtration is concentrated to small volume. The title compound crystallizes on cooling. Yield: 0.24 g, m.p. 208°-209° C.

Workup

  1. additionA mixture of 0.250 g
  2. filtrationafter filtration
  3. concentrationis concentrated to small volume
  4. customThe title compound crystallizes
  5. temperatureon cooling

Sources & evidence

ORD record
ord-2752f34f108c41339ac7b1ed499c1c8c
Source dataset
uspto-grants-1976_10
Patent number
US03987053

Linked notes

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