Methyl iodide → 1,3,5-Triazino(1,2-a)benzimidazol-4(3H)-one, 2,10-dihydro-2,2,3,10-tetramethyl-

HRID 615092Notes

Reaction equation

HRID 615092 reaction equation
[CH3:1][C:2]1([CH3:17])[N:10]([CH3:11])[C:9](=[O:12])[N:8]2[C:4](=[N:5][C:6]3[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=32)[NH:3]1.CI.[C:20](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C:2]1([CH3:17])[N:10]([CH3:11])[C:9](=[O:12])[N:8]2[C:4]([N:5]([CH3:20])[C:6]3[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=32)=[N:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 1591201,2-dihydro-2,2,3-trimethyl-1,3,5-triazino[1,2-a]benzimidazol-4(3H)-one

Product 1

HCID 1591111,3,5-Triazino(1,2-a)benzimidazol-4(3H)-one, 2,10-dihydro-2,2,3,10-tetramethyl-Yield 101.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2.0 g (0.0087 mole) 1,2-dihydro-2,2,3-trimethyl-1,3,5-triazino[1,2-a]benzimidazol-4(3H)-one, 1.1 ml (0.0174 mole) methyl iodide, anhydrous potassium carbonate (1 gram) and acetone (100 ml) was heated under reflux, with stirring, overnight. After refluxing had continued 21 hours an additional 1 ml of methyl iodide was added and solids removed from the mixture by suction filtration. The filtrate was evaporated under reduced pressure and the resulting residue dissolved in ethyl acetate, washed with water, then with brine and dried over MgSO4, filtered and solvent stripped off to give 1.8 g of crude product. Purification by high pressure liquid chromatography gave a solid, mp 79°-82° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureAfter refluxing
  4. waithad continued 21 hours
  5. customsolids removed from the mixture by suction filtration
  6. customThe filtrate was evaporated under reduced pressure
  7. dissolutionthe resulting residue dissolved in ethyl acetate
  8. washwashed with water
  9. dry with materialwith brine and dried over MgSO4
  10. filtrationfiltered

Sources & evidence

ORD record
ord-3cd249cd169e49d49b0953154bdab7d9
Source dataset
uspto-grants-1985_02
Patent number
US04497650

Reaction notes

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