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

HRID 1285079Notes

Reaction equation

HRID 1285079 reaction equation
[C:1](=[O:4])(O)[O-].[Na+].[N:6]1[C:13](Cl)=[N:12][C:10](Cl)=[N:9][C:7]=1[Cl:8].[CH3:15][OH:16]>O>[Cl:8][C:7]1[N:9]=[C:10]([O:16][CH3:15])[N:12]=[C:13]([O:4][CH3:1])[N:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 7954Cyanuric chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineYield 54.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a vigorously-stirred suspension of 54.6 g of sodium bicarbonate in 146 g of methanol and 16 ml water was added 60.0 g of cyanuric chloride in portions over a period of 30 minutes. The temperature rose to 30°-35° C. and, following the addition, was allowed to drop to 25° C. and the mixture was then heated to 50°±2° C. for 21/2 hours. The solution was allowed to cool and 600 ml ice-water was added and stirred for 15 minutes. Filtration of the thick reaction mixture followed by crystallization from hot hexanes gave 31.3 g of 2-chloro-4,6-dimethoxy-1,3,5-triazine as a colorless crystalline solid, m.p. 76°-78° C.

Workup

  1. customrose to 30°-35° C.
  2. additionthe addition
  3. customto drop to 25° C.
  4. temperaturethe mixture was then heated to 50°±2° C. for 21/2 hours
  5. temperatureto cool
  6. filtrationFiltration of the thick reaction mixture
  7. customfollowed by crystallization from hot hexanes

Sources & evidence

ORD record
ord-f152e72366f94976aa860adfb9f2691e
Source dataset
uspto-grants-1986_01
Patent number
US04565567

Reaction notes

Loading…