Ethanol → HCID 23462461, compound

HRID 224502Notes

Reaction equation

HRID 224502 reaction equation
C[O-].[Na+].[C:4]([O:11][CH2:12][CH3:13])(=[O:10])[C:5]([O:7]CC)=O.C(O)C.[CH3:17][N:18]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][N:20]=[C:19]1[CH3:26]>CO>[CH3:17][N:18]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][N:20]=[C:19]1[CH2:26][C:5](=[O:7])[C:4]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 3090DimetridazoleHCID 7268Diethyl OxalateHCID 10942334Sodium Methoxide

Product 1

HCID 23462461HCID 23462461, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 180 parts of a 30 percent strength by weight sodium methylate solution in methanol, 146 parts of diethyl oxalate and 150 parts by volume of ethanol is added in the course of 30 minutes, at 60° C., to a suspension of 141 parts of 1,2-dimethyl-5-nitroimidazole in 250 parts by volume of ethanol. After stirring for one hour at 60° C., the mixture is cooled and the sodium enolate of ethyl 1-methyl-5-nitroimidazol-2-yl-pyruvate is filtered off. The salt is then introduced into 1,300 parts by volume of 3 percent strength by weight hydrochloric acid, whilst stirring. The mixture is stirred for a further half-hour and the product is then filtered off. 190 parts (79% of theory) of ethyl 1-methyl-5-nitroimidazol-2-yl-pyruvate of melting point 141° C. (after recrystallization from ethanol) are obtained.

Workup

  1. temperaturethe mixture is cooled
  2. filtrationthe sodium enolate of ethyl 1-methyl-5-nitroimidazol-2-yl-pyruvate is filtered off
  3. additionThe salt is then introduced into 1,300 parts by volume of 3 percent strength by weight hydrochloric acid
  4. stirringwhilst stirring
  5. stirringThe mixture is stirred for a further half-hour
  6. filtrationthe product is then filtered off
  7. custom190 parts (79% of theory) of ethyl 1-methyl-5-nitroimidazol-2-yl-pyruvate of melting point 141° C. (after recrystallization from ethanol)
  8. customare obtained

Sources & evidence

ORD record
ord-b02e3eb2af5243298134166cdebaa0da
Source dataset
uspto-grants-1980_11
Patent number
US04232165

Reaction notes

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