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

HRID 1678437Notes

Reaction equation

HRID 1678437 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5]([Cl:6])=[N:4][C:2]=1[Cl:3].[C:10]1([Mg]Br)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[Cl:3][C:2]1[N:4]=[C:5]([Cl:6])[N:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:1]=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

To a solution of cyanuric chloride (18.0 g, 97.6 mmol, 1.00 equiv) in THF was added phenylmagnesium bromide (97.6 ml of a 1.0 M solution in THF, 97.6 mmol, 1.00 equiv), dropwise, at 0° C. After the addition the mixture was stirred at room temperature for 1 h (monitored by TLC). The reaction mixture was poured onto ice and stirred at room temperature for 30 min. The product was extracted with ethyl acetate, and the combined organic extracts were washed with aqueous sodium chloride. The ethyl acetate extracts were then dried (over Na2SO4), and concentrated to afford 16 g of the title compound. The crude product was carried forward without purification.

Workup

  1. additionAfter the addition the mixture
  2. additionThe reaction mixture was poured onto ice
  3. stirringstirred at room temperature for 30 min
  4. extractionThe product was extracted with ethyl acetate
  5. washthe combined organic extracts were washed with aqueous sodium chloride
  6. dry with materialThe ethyl acetate extracts were then dried (over Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e4d085ef6d1e4665988207a67cc2d332
Source dataset
uspto-grants-2011_08
Patent number
US08008483B2

Reaction notes

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