Methane → Etandazole

HRID 1757949Notes

Reaction equation

HRID 1757949 reaction equation
[N+:1]([C:4]1[N:5]([CH2:9][C:10]([O:12]C)=O)[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[CH2:14]([CH2:16][NH2:17])[OH:15].C>CO.C(O)C>[OH:15][CH2:14][CH2:16][NH:17][C:10](=[O:12])[CH2:9][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 297MethaneHCID 700EthanolamineHCID 89851Methyl 2-nitroimidazole-1-acetate

Product 1

HCID 3276EtandazoleYield 62.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 2.50 g (13.5 mmol) of methyl 2-nitroimidazole-1-acetate and 3.0 ml (50.0 mmol) of ethanolamine in 15.0 ml methanol was stirred 20 hr at room temperature. The mixture was diluted with 45 ml ethanol and heated on a stream bath to effect solution. The hot solution was decolorized with charcoal, filtered and evaporated to dryness. The residue was recrystallized from a solution of 150 ml ethyl acetate and 10 ml of methanol to afford 1.81 g (62.4%) of SR-2508 as a white powder, mp 164.5-165.0° C., that was homogeneous by thin layer chromatography on silica gel with 10% methanol in ethyl acetate (Rf 0.16). The solubility of SR-2508 in 0.9% saline solution was approximately 200 mg/ml.

Workup

  1. temperatureheated on a stream bath
  2. filtrationfiltered
  3. customevaporated to dryness
  4. customThe residue was recrystallized from a solution of 150 ml ethyl acetate and 10 ml of methanol

Sources & evidence

ORD record
ord-744061f907ff429c8b7e93b97e248ae9
Source dataset
uspto-grants-1983_02
Patent number
US04371540

Reaction notes

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