1,2-Dimethoxyethane → 1-Methyl-2-nitro-1H-imidazole-5-carboxaldehyde

HRID 1288028

Reaction equation

HRID 1288028 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]=C)=[CH:5][N:4]=[C:3]1[N+:9]([O-:11])=[O:10].C[O:13]CCOC>O=[Os](=O)(=O)=O.O>[CH3:1][N:2]1[C:6]([CH:7]=[O:13])=[CH:5][N:4]=[C:3]1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 2

HCID 80711,2-DimethoxyethaneHCID 932151-ME-2-NO2-5-Vinyl imidazole

Product 1

HCID 1003901-Methyl-2-nitro-1H-imidazole-5-carboxaldehydeYield 63%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

To a solution of 0.67 g. of 1-methyl-2-nitro-5-vinylimidazole in 20 ml. of 1,2-dimethoxyethane, a solution of 2 g. of NaIO4 in 5 ml. of water, followed by 0.025 g. of OsO4 is added with stirring at room temperature. After stirring for four hours, the mixture is allowed to stand overnight. The residue which is obtained by evaporation of the reaction medium to dryness under vacuum is extracted with ethyl acetate. The resulting solution after filtering is concentrated, yielding 0.43 g. of a product which, after crystallization from ethyl acetate, melts at 114°-115° C. Yield 63%.

Workup

  1. stirringAfter stirring for four hours
  2. customThe residue which is obtained by evaporation of the reaction medium to dryness under vacuum
  3. extractionis extracted with ethyl acetate
  4. filtrationThe resulting solution after filtering
  5. concentrationis concentrated
  6. customyielding 0.43 g
  7. customof a product which, after crystallization from ethyl acetate, melts at 114°-115° C

Sources & evidence

ORD record
ord-958bac4161344cff9c486501b571a860
Source dataset
uspto-grants-1976_10
Patent number
US03987053

Linked notes

Loading…