Methanol → 2-Chloro-4,6-dimethoxy-1,3,5-triazine
Reaction equation
[C:1](=[O:4])([O-])O.[Na+].[CH3:6][OH:7].O.[N:9]1[C:16](Cl)=[N:15][C:13](Cl)=[N:12][C:10]=1[Cl:11]>>[Cl:11][C:10]1[N:12]=[C:13]([O:7][CH3:6])[N:15]=[C:16]([O:4][CH3:1])[N:9]=1Participants
Conditions
- Temperature
- 10 °C
Procedure
In a 500-ml four-necked flask equipped with a stirrer and a thermometer, 63.0 g (0.75 mol) of sodium hydrogencarbonate, 98.5 g (3.08 mol, water content: 187 ppm) of methanol and 12.1 g (0.675 mol) of water were placed. With stirring at a temperature of not higher than 10° C., 46.1 g (0.25 mol) of cyanuric chloride was added, followed by stirring for 30 minutes. Then, the reaction was conducted at 35° C. for 15 hours. The weight of the reaction solution from which a salt formed had been removed was 158 g, and the water content was 143,000 ppm. After cooling, methanol was distilled off. To the residue, 400 ml of water was added, and the objective product was extracted with 300 ml of ethyl acetate. The organic layer was washed with 100 ml of water and then vacuum concentrated to obtain 29.5 g of 2-chloro-4,6-dimethoxy-1,3,5-triazine. The yield was 67.2%. From the gas chromatography analysis, the purity proved to be 94.0% (% by area).
Workup
- customIn a 500-ml four-necked flask equipped with a stirrer
- stirringby stirring for 30 minutes
- customThe weight of the reaction solution from which a salt formed
- customhad been removed
- temperatureAfter cooling
- distillationmethanol was distilled off
- additionTo the residue, 400 ml of water was added
- extractionthe objective product was extracted with 300 ml of ethyl acetate
- washThe organic layer was washed with 100 ml of water
- concentrationvacuum concentrated
Sources & evidence
- ORD record
- ord-1d43b00eb58a475b85c1923b285ec42f
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06673922B2
Reaction notes
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