O-Phenylenediamine → HCID 21883720, Verbindung

HRID 722320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 722320
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=O)[C:5]2[O:10][CH:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][C:6]=2[CH:20]=1.[C:23]1([NH2:30])[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH2:29]>[N+](C1C=CC=CC=1)([O-])=O>[NH:29]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:30]=[C:21]1[C:4]1[C:5]2[O:10][CH:9]([C:11]([F:12])([F:14])[F:13])[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][C:6]=2[CH:20]=[C:2]([Cl:1])[CH:3]=1

Komponenten

4

Edukt 2

HCID 7243O-PhenylenediamineHCID 21883599HCID 21883599, Verbindung

Produkt 1

HCID 21883720HCID 21883720, VerbindungAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7416NitrobenzeneLösungsmittel

Versuchsvorschrift

A solution of the aldehyde (Example 76, Step 3) (0.33 g, 0.99 mmol) and 1,2-phenylenediamine (0.11 g, 1.02 mmol) in nitrobenzene (20 mL) was heated to 150° C. for 1.8 hours. The reaction mixture was extracted with ethyl acetate, washed with brine, dried over MgSO4, and concentrated in vacuo and purified by flash chromatography over silica gel (with 1:9 ethyl acetate/hexane as eluant) to give the ester as a brown solid (0.18 g, 43%) which was used in the next step without further purification.

Aufarbeitung

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography over silica gel (with 1:9 ethyl acetate/hexane as eluant)

Quellen und Nachweise

ORD-Eintrag
ord-c94cef33dfc1422d82b19bd1e7dcb7ad
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138411B2

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