Methyl Isocyanate → 4-Ethyl-5-(N-methyl-carbamoyl)-4,5,6,7-tetrahydro-imidazo-[4,5-c]-pyridine

HRID 1391220Notes

Reaction equation

HRID 1391220 reaction equation
[CH2:1]([CH:3]1[C:8]2[N:9]=[CH:10][NH:11][C:7]=2[CH2:6][CH2:5][NH:4]1)[CH3:2].[CH3:12][N:13]=[C:14]=[O:15]>O1CCOCC1.C(OCC)(=O)C>[CH2:1]([CH:3]1[C:8]2[N:9]=[CH:10][NH:11][C:7]=2[CH2:6][CH2:5][N:4]1[C:14](=[O:15])[NH:13][CH3:12])[CH3:2]

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 233422924-Ethyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine

Product 1

HCID 213307364-Ethyl-5-(N-methyl-carbamoyl)-4,5,6,7-tetrahydro-imidazo-[4,5-c]-pyridine

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1.51 g of 4-ethyl-4,5,6,7-tetrahydro-imidazo-[4,5-c]-pyridine and 2.28 g of methyl isocyanate in 20 ml of dry dioxane is refluxed for 1.5 h. The solution is cooled and filtered. The solid collected is dissolved in 30 ml of methanol and treated with 7 ml of 2N sodium hydroxide for 2 h at room temperature. After neutralization the solution is extracted with chloroform. Evaporation of the solvent leaves a residue that is taken up in ethyl acetate. 1.05 g of the title compound, m.p. 240°, are collected.

Workup

  1. temperatureThe solution is cooled
  2. filtrationfiltered
  3. customThe solid collected
  4. dissolutionis dissolved in 30 ml of methanol
  5. additiontreated with 7 ml of 2N sodium hydroxide for 2 h at room temperature
  6. extractionAfter neutralization the solution is extracted with chloroform
  7. customEvaporation of the solvent
  8. customleaves a residue that
  9. custom1.05 g of the title compound, m.p. 240°, are collected

Sources & evidence

ORD record
ord-f5cfd79cde424ff9a634ee4cc70110bf
Source dataset
uspto-grants-1979_02
Patent number
US04141899

Reaction notes

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