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

HRID 1922017Notes

Reaction equation

HRID 1922017 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:9]1[C:16]([Cl:17])=[N:15][C:13](Cl)=[N:12][C:10]=1[Cl:11]>C1COCC1>[Cl:11][C:10]1[N:9]=[C:16]([Cl:17])[N:15]=[C:13]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:12]=1

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 178418255HCID 178418255, compound

Product 1

HCID 155492,4-Dichloro-6-phenyl-1,3,5-triazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Phenylmagnesium bromide (97.6 ml of a 1.0 M solution in THF, 97.6 mmol, 1.0 equiv) was added dropwise to a THF (8 mL) solution of cyanuric chloride (18.0 g, 97.6 mmol, 1.0 equiv) at 0° C. The reaction mixture was stirred at room temperature for 1 h and was poured onto ice and stirred for 30 min. The product was extracted with ethyl acetate, and the combined organic layers were washed with (sat.) sodium chloride, dried (Na2SO4), filtered, and concentrated under reduced pressure to afford 16 g the title compound. The crude product was carried forward without purification.

Workup

  1. additionwas poured onto ice
  2. stirringstirred for 30 min
  3. extractionThe product was extracted with ethyl acetate
  4. washthe combined organic layers were washed with (sat.) sodium chloride
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4af47e1b50ab4854948a8c44c1aa6cec
Source dataset
uspto-grants-2012_05
Patent number
US08173805B2

Reaction notes

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