HCID 12519460, compound → 1H-Imidazole-2-carboxaldehyde, 1-[2-(acetyloxy)ethyl]-5-nitro-

HRID 1730179Notes

Reaction equation

HRID 1730179 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]=[C:8]1[CH2:15][OH:16])(=[O:3])[CH3:2].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C1C=CC=CC=1>[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[CH:15]=[O:16])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 12519460HCID 12519460, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 122143961H-Imidazole-2-carboxaldehyde, 1-[2-(acetyloxy)ethyl]-5-nitro-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A 6.27 gm. portion of 1-(2-acetoxyethyl)-2-hydroxymethyl-5-nitroimidazole is refuxed with 13.3 gm. of lead tetraacetate in 200 ml. of benzene for 18 hours, cooled, and filtered. The filtrate is washed with 50 ml. of saturated sodium carbonate solution, and the organic phase is separated therefrom. The remaining aqueous phase is twice extracted with 30 ml. of chloroform, and then combined with the above separated organic phase. The combined organic phases are dried under magnesium sulfate, and filtered. The organic solvents are then removed in vacuo, giving the above aldehyde.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. washThe filtrate is washed with 50 ml
  4. customof saturated sodium carbonate solution, and the organic phase is separated
  5. extractionThe remaining aqueous phase is twice extracted with 30 ml
  6. customThe combined organic phases are dried under magnesium sulfate
  7. filtrationfiltered
  8. customThe organic solvents are then removed in vacuo

Sources & evidence

ORD record
ord-e332d46006a34ad09369d53fbe031e53
Source dataset
uspto-grants-1976_11
Patent number
US03991200

Reaction notes

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