Carbon Dioxide → 2,4-Dichloro-6-methoxy-3,5-triazine

HRID 848815Notes

Reaction equation

HRID 848815 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5]([Cl:6])=[N:4][C:2]=1Cl.CO.[C:12](=O)(O)[O-:13].[Na+].C(=O)=O>O>[CH3:12][O:13][C:2]1[N:4]=[C:5]([Cl:6])[N:7]=[C:8]([Cl:9])[N:1]=1

Participants

6

Reactant 4

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

Product 1

HCID 192672,4-Dichloro-6-methoxy-3,5-triazineYield 54.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
3 °C

Procedure

36.8 g (0.2 mol) of cyanuric chloride are added in the course of 2 hours, at 0°-5° C., to a mixture of 200 ml of methanol, 25 ml of water and 33.6 g (0.4 mol) of sodium bicarbonate. The reaction mixture is stirred, first for one hour at about 3° C. and then for about 30 minutes at 30° C., until the evolution of CO2 has ceased. The white suspension is washed with 100 ml of water and the product is filtered off and dried at 60° C. in a drying cabinet. Recrystallisation from hexane yields 19.6 g of 2-methoxy-4,6-dichloro-1,3,5-triazine with a melting point at about 90° C.

Workup

  1. waitfor about 30 minutes at 30° C.
  2. washThe white suspension is washed with 100 ml of water
  3. filtrationthe product is filtered off
  4. customdried at 60° C. in a drying cabinet
  5. customRecrystallisation from hexane

Sources & evidence

ORD record
ord-f8fd2639e92640e69000d2a76362181f
Source dataset
uspto-grants-1981_10
Patent number
US04297492

Reaction notes

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