Benzaldehyde → HCID 218198, compound

HRID 1288029Notes

Reaction equation

HRID 1288029 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][N:4]=[C:3]1[N+:8]([O-:10])=[O:9].[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[K].CC(C)([O-])C>C(O)C>[CH3:1][N:2]1[C:6]([CH:7]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][N:4]=[C:3]1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 78888Imidazole, 1,5-dimethyl-2-nitro-HCID 45749132-Methylpropan-2-olateHCID 5462222Potassium

Product 1

HCID 218198HCID 218198, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7.2 g. of 1,5-dimethyl-2-nitroimidazole, 41.2 ml. of benzaldehyde and 7.9 g. of potassium dazole, tert-butoxide in 300 ml. of ethanol is refluxed for 35 minutes under nitrogen. The residue, which is obtained by evaporation of the reaction mixture under vacuum, is extracted with ethyl ether and filtered. The ethyl ether solution after concentration yields an oily residue which is chromatographed through 300 g. of silica gel by eluting with chloroform. After evaporation of the solvent under vacuum at 40° C., an oily residue is obtained which crystallizes on standing. After washing with a small amount of methyl ethyl ketone, 1.9 g. (16%) of a product which melts at 170°-180° C. is obtained.

Workup

  1. additionA mixture of 7.2 g
  2. customThe residue, which is obtained by evaporation of the reaction mixture under vacuum
  3. extractionis extracted with ethyl ether
  4. filtrationfiltered
  5. concentrationThe ethyl ether solution after concentration
  6. customyields an oily residue which
  7. customis chromatographed through 300 g
  8. washof silica gel by eluting with chloroform
  9. customAfter evaporation of the solvent under vacuum at 40° C.
  10. customan oily residue is obtained which
  11. customcrystallizes
  12. washAfter washing with a small amount of methyl ethyl ketone, 1.9 g

Sources & evidence

ORD record
ord-9ea875502ae94d9d988a1803e6727c4e
Source dataset
uspto-grants-1976_10
Patent number
US03987053

Reaction notes

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