Dimethyl Sulfate → HCID 21437373, compound

HRID 2397218Notes

Reaction equation

HRID 2397218 reaction equation
[CH2:1]([C:9]1[NH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][N:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].S(OC)(O[CH3:21])(=O)=O>C(O)=O>[CH3:21][N:10]1[C:11]([N+:14]([O-:16])=[O:15])=[CH:12][N:13]=[C:9]1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 21437372HCID 21437372, compound

Product 1

HCID 21437373HCID 21437373, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

225 parts of 2-octyl-5-nitroimidazole is boiled under reflux with 500 parts of formic acid and 126 parts of dimethyl sulfate for 4 hours, the formic acid is distilled off in vacuo and 500 parts of water is added to the residue. The unreacted 2-octyl-5-nitroimidazole (72 parts) is separated and the aqueous phase is adjusted with aqueous ammonia solution to pH 10 so that the 1-methyl-2-octyl-5-nitroimidazole separates as an oily substance. The crude product is dissolved in ether and saturated with hydrogen chloride while cooling. 123 parts of 1-methyl-2-octyl-5-nitroimidazole having a melting point of 141° C. is obtained and this is equivalent to a yield of 66% of theory based on the 2-octyl-5-nitroimidazole reacted.

Workup

  1. distillationthe formic acid is distilled off in vacuo and 500 parts of water
  2. additionis added to the residue
  3. customThe unreacted 2-octyl-5-nitroimidazole (72 parts) is separated
  4. dissolutionThe crude product is dissolved in ether and saturated with hydrogen chloride
  5. temperaturewhile cooling

Sources & evidence

ORD record
ord-8dc3c678d9dd4050b0cbb820ff4aa591
Source dataset
uspto-grants-1977_05
Patent number
US04021442

Reaction notes

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