Acetic Acid → 5,8-Dibromo-2,3-diphenylquinoxaline

HRID 1912212

Reaktionsgleichung

Reaktionsgleichung von HRID 1912212
[Br:1][C:2]1[C:3]([NH2:10])=[C:4]([NH2:9])[C:5]([Br:8])=[CH:6][CH:7]=1.C(O)(=O)C.[C:15]1([C:21]([C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=O)=O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)(O)[O-].[Na+]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[C:4]2[C:3]=1[N:10]=[C:21]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[N:9]2

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8651BenzilHCID 516892Sodium BicarbonateHCID 118215323,6-Dibromobenzene-1,2-diamine

Produkt 1

HCID 224759015,8-Dibromo-2,3-diphenylquinoxalineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Preparation procedure: 3,6-dibromo-o-phenylene diamine (1.0 g, 3.7 mmol) is added to an acetic acid (20 mL) solution of benzil (0.39 g, 1.84 mmol) at 120° C. The resulting solution is mixed homogeneously and reflux for 12 hours. The reaction solution is poured into water, neutralized with sodium bicarbonate, extracted with chloroform, washed with saturated brine water, and dried over anhydrous sodium sulfate. The solvents are removed using a rotary evaporator. The crude product is subjected to column chromatography to give a white solid, which is then recrystallized in chloroform/n-hexane to afford a white solid powder (yield 86%), MALDI-TOF-MS (m/z): 440.1 (M+).

Aufarbeitung

  1. customPreparation procedure
  2. additionThe resulting solution is mixed homogeneously
  3. temperaturereflux for 12 hours
  4. extractionextracted with chloroform
  5. washwashed with saturated brine water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvents are removed
  8. customa rotary evaporator
  9. customto give a white solid, which
  10. customis then recrystallized in chloroform/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-f2dc75123a7d4ef98313fa61a8cd868e
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604147B2

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