P-Phenylenediamine → HCID 57756220, Verbindung

HRID 227827

Reaktionsgleichung

Reaktionsgleichung von HRID 227827
[C:1]1([NH2:8])[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1.Cl[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:12][N:11]=1>O>[C:20]1([C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]([NH:7][C:4]3[CH:5]=[CH:6][C:1]([NH2:8])=[CH:2][CH:3]=3)=[N:11][N:12]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Komponenten

4

Edukt 2

HCID 7814P-PhenylenediamineHCID 2721091-Chloro-4-phenylphthalazine

Produkt 1

HCID 57756220HCID 57756220, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Benzene-1,4-diamine (0.337 g, 3.12 mmol) and 1-chloro-4-phenylphthalazine (0.500 g, 2.08 mmol) were treated with 7.5 mL 2-BuOH in a sealed tube and heated to 110° C. The reaction quickly became a solid, yellow mass. After several hours, the reaction was cooled and diluted with water. The slurry was then partitioned between DCM and 1N NaOH. The aqueous layer was extracted into DCM (2×). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resulting material was purified by silica gel chromatography, ISCO, 40 g, 0-10% MeOH/MC to give N1-(4-phenylphthalazin-1-yl)benzene-1,4-diamine as an orange-brown solid. MS m/z=313 [M+H]+. Calc'd for C20H16N4: 312.4.

Aufarbeitung

  1. customThe reaction
  2. waitAfter several hours
  3. temperaturethe reaction was cooled
  4. customThe slurry was then partitioned between DCM and 1N NaOH
  5. extractionThe aqueous layer was extracted into DCM (2×)
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting material was purified by silica gel chromatography, ISCO, 40 g, 0-10% MeOH/MC

Quellen und Nachweise

ORD-Eintrag
ord-6075b051e6e9493d9a18c6d2569faf92
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560551B2

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