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

HRID 268153Notes

Reaction equation

HRID 268153 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-triazineYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 45 g. of methanol and 5 g. of water were added 16.8 g. (0.2 mole) of sodium bicarbonate and 18.5 g. (0.1 mole) of cyanuric chloride. Carbon dioxide was liberated at a moderate rate as the temperature rose to 35°C. The mixture was refluxed for 30 minutes after gas evolution had nearly ceased. It was then cooled, diluted with water, and filtered. The crystalline product was washed with water until chloride free and was dried in a vacuum desiccator. The crude product weighed 13 g. (74% yield), m.p. 74°-76°C. Recrystallization from heptane gave m.p. 75°-76°C.

Workup

  1. customrose to 35°C
  2. temperatureThe mixture was refluxed for 30 minutes after gas evolution
  3. temperatureIt was then cooled
  4. filtrationfiltered
  5. washThe crystalline product was washed with water until chloride free
  6. customwas dried in a vacuum desiccator
  7. customRecrystallization from heptane
  8. customgave m.p. 75°-76°C.

Sources & evidence

ORD record
ord-f970e3d764cf4e9b8bf3cd0392a4e421
Source dataset
uspto-grants-1976_03
Patent number
US03947374

Reaction notes

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