Cyanuric chloride → 2,4-Dichloro-6-(4-methoxyphenyl)(1,3,5)triazine

HRID 493015Notes

Reaction equation

HRID 493015 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5]([Cl:6])=[N:4][C:2]=1[Cl:3].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([Mg])=[CH:14][CH:13]=1>C1COCC1>[Cl:3][C:2]1[N:4]=[C:5]([Cl:6])[N:7]=[C:8]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)[N:1]=1

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 178491920HCID 178491920, compound

Product 1

HCID 110105692,4-Dichloro-6-(4-methoxyphenyl)(1,3,5)triazineYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
7.5 °C

Procedure

A 1-litre reactor is charged under nitrogen with cyanuric chloride (36.9 g, 0.2 mol) and then with 50 ml of THF. The suspension is cooled to 5-10° C. With stirring, at a temperature of less than 10° C., a 0.5M solution of para-methoxyphenylmagnesium in THF (400 ml, 0.2 mol) is run in under inert gas over 45 minutes. The reaction mixture is left to stand overnight. The solvent is evaporated on a rotary evaporator. The residue is poured into acidified water. Following extraction with dichloromethane, the organic phase is washed with water and dried over sodium sulphate. The solvent is evaporated. The crude solid obtained is triturated with isopropanol and then filtered. The solid is dissolved in hot toluene. Addition of the same volume of heptane precipitates the product. The precipitate is cooled, isolated by filtration and dried. This gives 31.7 g (yield: 62%) of 2,4-dichloro-6-(4-methoxyphenyl)[1,3,5]triazine in the form of a beige powder (m.p. 133-136° C.), which is used as it is in the following step.

Workup

  1. waitThe reaction mixture is left
  2. customThe solvent is evaporated on a rotary evaporator
  3. additionThe residue is poured
  4. extractionextraction with dichloromethane
  5. washthe organic phase is washed with water
  6. dry with materialdried over sodium sulphate
  7. customThe solvent is evaporated
  8. customThe crude solid obtained
  9. customis triturated with isopropanol
  10. filtrationfiltered
  11. dissolutionThe solid is dissolved in hot toluene
  12. additionAddition of the same volume of heptane
  13. customprecipitates the product
  14. temperatureThe precipitate is cooled
  15. customisolated by filtration
  16. customdried

Sources & evidence

ORD record
ord-604ea78807fc44fb91d4329633a70fd1
Source dataset
uspto-grants-2009_05
Patent number
US07534421B2

Reaction notes

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