Methyl 1-methyl-4,5-dihydro-1H-imidazole-4-carboxylate → METHYL 1-METHYL-1H-IMIDAZOLE-4-CARBOXYLATE

HRID 1721824Notes

Reaction equation

HRID 1721824 reaction equation
[CH3:1][N:2]1[CH2:6][CH:5]([C:7]([O:9][CH3:10])=[O:8])[N:4]=[CH:3]1>C(O)C.C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:4]=[CH:3]1

Participants

5

Reactant 1

HCID 17776183Methyl 1-methyl-4,5-dihydro-1H-imidazole-4-carboxylate

Product 1

HCID 2773510METHYL 1-METHYL-1H-IMIDAZOLE-4-CARBOXYLATE

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

19.0 g of manganese dioxide was added to a stirred solution of 4.7 g of 38D in ethanol-free, chloroform and the mixture was stirred overnight at room temperature. The mixture was heated at reflux for 1 hour, cooled, 9.5 g of manganese dioxide was added; the mixture was stirred at room temperature for 2 hours and at reflux for 30 minutes. The mixture was cooled and filtered and the filtrate was stripped of solvent to give methyl 1-methylimidazole-4-carboxylate (38E), as a yellow solid, m.p.: 72.5°-81° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. temperaturecooled
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. temperatureat reflux for 30 minutes
  6. temperatureThe mixture was cooled
  7. filtrationfiltered

Sources & evidence

ORD record
ord-20cdcc39394d432e9b55bc1583a27fa5
Source dataset
uspto-grants-1989_08
Patent number
US04853027

Reaction notes

Loading…