Cyanuric chloride → 2,4-Dichloro-6-methyl-1,3,5-triazine

HRID 1678435Notes

Reaction equation

HRID 1678435 reaction equation
[CH3:1][Mg]Br.[N:4]1[C:11](Cl)=[N:10][C:8]([Cl:9])=[N:7][C:5]=1[Cl:6]>CCOCC.C1COCC1>[Cl:6][C:5]1[N:7]=[C:8]([Cl:9])[N:10]=[C:11]([CH3:1])[N:4]=1

Participants

5

Reactant 2

HCID 7954Cyanuric chlorideHCID 178418573HCID 178418573, compound

Product 1

HCID 160832,4-Dichloro-6-methyl-1,3,5-triazineYield 34%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromide (9.00 mL of a 3.0 M solution in Et2O, 27.1 mmol, 1.00 equiv) was added dropwise over 1 h to a cooled (0° C.) solution of cyanuric chloride (5.00 g, 27.1 mmol, 1.00 equiv) in THF (270 mL). The reaction mixture was stirred at room temperature overnight and was then quenched with sat NH4Cl (aq). The aqueous layer was extracted 3 times using ethyl acetate, and the combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified using silica gel chromatography (0-40% CH2Cl2/hexanes) to afford 1.5 g (34%) of the title compound. MS (ES+): m/e 164.0 [M+H]+.

Workup

  1. customwas then quenched with sat NH4Cl (aq)
  2. extractionThe aqueous layer was extracted 3 times
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-289252b656534cd1b38f0f8f1cef3e28
Source dataset
uspto-grants-2011_08
Patent number
US08008483B2

Reaction notes

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