Formaldehyde → HCID 12519460, compound

HRID 596203Notes

Reaction equation

HRID 596203 reaction equation
[C:1]([O:4][CH2:5][CH2:6][N:7]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][N:9]=[CH:8]1)(=[O:3])[CH3:2].[CH2:15]=[O:16]>CS(C)=O>[C:1]([O:4][CH2:5][CH2:6][N:7]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][N:9]=[C:8]1[CH2:15][OH:16])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 12519458HCID 12519458, compound

Product 1

HCID 12519460HCID 12519460, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 24.25 g. of 1-(2'-acetoxyethyl)-5-nitroimidazole prepared as in Example 4, 15 g. of paraformaldehyde and 150 ml. of dimethylsulfoxide is heated in a sealed tube overnight at 100°-150° C. The dimethylsulfoxide is removed completely at reduced pressure, and the residue is dissolved in water and extracted with chloroform. The chloroform extract is dried and concentrated. The residue is dissolved in ethyl acetate, and the solution is charged on a column of alumina. Elution with ethyl acetate and evaporation of the solvent yields 1-(2'-acetoxyethyl)-2-hydroxymethyl-5-nitroimidazole, m.p. 38°-145° C.

Workup

  1. additionA mixture of 24.25 g
  2. customThe dimethylsulfoxide is removed completely at reduced pressure
  3. dissolutionthe residue is dissolved in water
  4. extractionextracted with chloroform
  5. extractionThe chloroform extract
  6. customis dried
  7. concentrationconcentrated
  8. dissolutionThe residue is dissolved in ethyl acetate
  9. additionthe solution is charged on a column of alumina
  10. washElution
  11. customwith ethyl acetate and evaporation of the solvent

Sources & evidence

ORD record
ord-b85caf51dd5e4d7db0ce14f4298bd5bb
Source dataset
uspto-grants-1977_03
Patent number
US04010176

Reaction notes

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