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

HRID 325752

반응식

HRID 325752 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4bf43c85562b43df8b7424e0a6d50c11
출처 데이터셋
uspto-grants-1984_04
특허 번호
US04442278

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