Cyanuric chloride → 2,4-Bis(4-ethynylphenyl)-6-phenyl-1,3,5-triazine

HRID 325752

Reaction equation

HRID 325752 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[C:10]1([Mg]Br)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C[Si](C)(C)[C:20]#[C:21][C:22]1[CH:27]=[CH:26][C:25](Br)=[CH:24][CH:23]=1.[Mg]>O1CCCC1>[C:10]1([C:2]2[N:4]=[C:5]([C:25]3[CH:26]=[CH:27][C:22]([C:21]#[CH:20])=[CH:23][CH:24]=3)[N:7]=[C:8]([C:25]3[CH:26]=[CH:27][C:22]([C:21]#[CH:20])=[CH:23][CH:24]=3)[N:1]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 7954Cyanuric chlorideHCID 4226980(4-Bromophenylethynyl)trimethylsilaneHCID 5462224MagnesiumHCID 178418255HCID 178418255, compound

Product 1

HCID 204296802,4-Bis(4-ethynylphenyl)-6-phenyl-1,3,5-triazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

One mole of cyanuric chloride was treated with one mole of phenylmagnesium bromide as described in Step I of Example I. The product of this reaction (2.3 g, 0.01 mole) in 25 ml of tetrahydrofuran (THF) was added slowly to a refluxing solution of the Grignard reagent prepared from 1-(trimethylsilyl)-2-(4-bromophenyl)acetylene (0.03 moles) and magnesium (0.75 g). The solution was stirred overnight, filtered, and the solvent removed. To the residue which remained was added a solution of KOH (10.0 g) in water (5 ml), anhydrous ethanol (100 ml) and dioxane (100 ml). The resulting mixture was heated for 2.5 hours at 60° C., filtered, and the solvent removed. Chromatographic separation of the resulting residue yielded a yellow solid, 6-phenyl-2,4-bis(4-ethynylphenyl)-s-triazine, which melted at approximately 215° C. with rapid polymerization.

Workup

  1. filtrationfiltered
  2. customthe solvent removed
  3. additionTo the residue which remained was added a solution of KOH (10.0 g) in water (5 ml), anhydrous ethanol (100 ml) and dioxane (100 ml)
  4. filtrationfiltered
  5. customthe solvent removed
  6. customChromatographic separation of the resulting residue

Sources & evidence

ORD record
ord-4bf43c85562b43df8b7424e0a6d50c11
Source dataset
uspto-grants-1984_04
Patent number
US04442278

Linked notes

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