Formic Acid → 1-Methyl-5-nitroimidazole

HRID 2397215

Reaction equation

HRID 2397215 reaction equation
[N+:1]([C:4]1[NH:8][CH:7]=[N:6][CH:5]=1)([O-:3])=[O:2].[CH:9](O)=O>S(OC)(OC)(=O)=O>[CH3:9][N:8]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][N:6]=[CH:7]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 182084-Nitroimidazole

Product 1

HCID 182101-Methyl-5-nitroimidazoleYield 82%

Reagents, catalysts & solvents 1

HCID 6497Dimethyl SulfateSolvent

Procedure

202 parts of 5-nitroimidazole is dissolved in 600 parts of formic acid (90% by weight), 250 parts of dimethyl sulfate is added and the whole is heated for 6 hours. The formic acid is distilled off in vacuo. 420 parts of water is added to the residue, the whole cooled to from 0° to 5° C. and the unreacted 5-nitroimidazole (60 parts) is centrifuged off. The mixture is adjusted to pH 10 with aqueous ammonia solution (25% by weight) and the precipitate is separated at 0° to 5° C. 130 parts of 1-methyl-5-nitroimidazole having a melting point of 58° to 60° C. is obtained; this is equivalent to a yield of 82% of theory based on reacted 4(5)-nitroimidazole.

Workup

  1. additionis added
  2. temperaturethe whole is heated for 6 hours
  3. distillationThe formic acid is distilled off in vacuo
  4. addition420 parts of water is added to the residue
  5. temperaturethe whole cooled to from 0° to 5° C.
  6. customthe precipitate is separated at 0° to 5° C

Sources & evidence

ORD record
ord-092cab30577549c3af8174dff40cb61c
Source dataset
uspto-grants-1977_05
Patent number
US04021442

Linked notes

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