Dimethyl Sulfate → Dimetridazole

HRID 2397214Notes

Reaction equation

HRID 2397214 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>[CH3:1][C:2]1[NH:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=1.[CH3:14][N:3]1[C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=[C:2]1[CH3:1]

Participants

5

Reactant 2

HCID 6497Dimethyl SulfateHCID 127602-Methyl-5-nitroimidazole

Product 2

HCID 3090DimetridazoleHCID 127602-Methyl-5-nitroimidazole

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
80 °C

Procedure

600 parts of formic acid (85%), 225 parts of 2-methyl-5-nitroimidazole and 250 parts of dimethyl sulfate are heated in a stirred vessel for 4 hours under reflux (80° C.). The formic acid is then distilled off in vacuo. The residue which remains is dissolved in 400 parts of water neutralized to pH 1.8 with aqueous ammonia solution and cooled to from 0° to +5° C. The unreacted 2-methyl-5-nitroimidazole is deposited and is centrifuged off. The mixture is then adjusted to pH 10 with aqueous ammonia solution and 1,2-dimethyl-5-nitroimidazole is separated at 10° C. 75 parts of 2-methyl-5-nitroimidazole and 145 parts of 1,2-dimethyl-5-nitroimidazole of the melting point 137° to 140° C. are obtained. The yield based on reacted 2-methyl-5-nitroimidazole is 87% of theory.

Workup

  1. distillationThe formic acid is then distilled off in vacuo
  2. dissolutionThe residue which remains is dissolved in 400 parts of water
  3. temperaturecooled to from 0° to +5° C
  4. customis separated at 10° C

Sources & evidence

ORD record
ord-baa896b97aea495dbeab2b6697049d1d
Source dataset
uspto-grants-1977_05
Patent number
US04021442

Reaction notes

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