Dimethyl Sulfate → Dimetridazole

HRID 2397219Notes

Reaction equation

HRID 2397219 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=1.S(OC)(O[CH3:14])(=O)=O>C(O)(=O)C>[CH3:14][N:3]1[C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=[C:2]1[CH3:1]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 127602-Methyl-5-nitroimidazole

Product 1

HCID 3090DimetridazoleYield 75.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

127 parts of 2-methyl-5-nitroimidazole, 350 parts of acetic acid and 126 parts of dimethyl sulfate are boiled under reflux for 4 hours. The acetic acid is distilled off in vacuo and the residue is dissolved in 500 parts of water and adjusted to pH 1.8 with aqueous ammonia solution. After cooling to from 0° to 5° C. the unreacted 2-methyl-5-nitroimidazole is suction filtered, the filtrate is adjusted to pH 10 and after cooling the 1,2-dimethyl-5-nitroimidazole is isolated. In addition to 30.4 parts of starting material (II) there is obtained 81 parts of 1,2-dimethyl-5-nitroimidazole (melting point 140° C.); this is equivalent to a yield of 75.5% of theory.

Workup

  1. temperatureunder reflux for 4 hours
  2. distillationThe acetic acid is distilled off in vacuo
  3. dissolutionthe residue is dissolved in 500 parts of water
  4. temperatureAfter cooling to from 0° to 5° C. the unreacted 2-methyl-5-nitroimidazole
  5. filtrationfiltered
  6. temperatureafter cooling the 1,2-dimethyl-5-nitroimidazole
  7. customis isolated

Sources & evidence

ORD record
ord-48997541e73a4ecc9328eab2d57bdb12
Source dataset
uspto-grants-1977_05
Patent number
US04021442

Reaction notes

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