Carbon Dioxide → 2-Chloro-4,6-dimethoxy-1,3,5-triazine

HRID 1885968Notes

Reaction equation

HRID 1885968 reaction equation
CO.[C:3](=[O:6])(O)[O-].[Na+].[N:8]1[C:15](Cl)=[N:14][C:12](Cl)=[N:11][C:9]=1[Cl:10].[C:17](=O)=[O:18]>O>[Cl:10][C:9]1[N:11]=[C:12]([O:18][CH3:17])[N:14]=[C:15]([O:6][CH3:3])[N:8]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 887MethanolHCID 7954Cyanuric chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred mixture of 45.0 grams of methanol and 5.0 grams of water was added 16.8 grams (0.2 mole) of sodium bicarbonate and 18.5 grams (0.1 mole) of cyanuric chloride. The addition caused the reaction mixture temperature to rise to 35° C. and the liberation of carbon dioxide gas. After the gas evolution slowed, the reaction mixture was heated to reflux where it stirred for 30 minutes. The reaction mixture was cooled, diluted with water, and the resultant solid was collected by filtration. The solid was washed repeatedly with water and dried to yield 13.0 grams of 2-chloro-4,6-dimethoxy-1,3,5-triazine, m.p. 74°-76° C. Recrystallization of the solid from heptane raised the melting point to 75°-76° C.

Workup

  1. additionThe addition
  2. customto rise to 35° C.
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux where it
  5. temperatureThe reaction mixture was cooled
  6. filtrationthe resultant solid was collected by filtration
  7. washThe solid was washed repeatedly with water
  8. customdried

Sources & evidence

ORD record
ord-b680ff45fb8a4c4a976e4690dfde8f15
Source dataset
uspto-grants-1992_09
Patent number
US05149357

Reaction notes

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