2-Chlorobenzoyl chloride → HCID 13457735, Verbindung

HRID 280118Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 280118
[C:1]1(=[O:16])[N:5]([N:6]2[CH:10]=[CH:9][CH:8]=[CH:7]2)[C:4](=[O:11])[C:3]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:2]12.[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>ClCCCl>[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([C:7]1[N:6]([N:5]2[C:4](=[O:11])[C:3]3=[CH:12][CH:13]=[CH:14][CH:15]=[C:2]3[C:1]2=[O:16])[CH:10]=[CH:9][CH:8]=1)=[O:21]

Komponenten

4

Edukt 2

HCID 691102-Chlorobenzoyl chlorideHCID 8537192-(1H-Pyrrol-1-yl)isoindoline-1,3-dione

Produkt 1

HCID 13457735HCID 13457735, VerbindungAusbeute 123,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a vigorously stirred mixture of 1-phthalimidopyrrole (45 g, 0.212 mol) and o-chlorobenzoyl chloride (37 g, 0.212 mol) in 500 ml of 1,2-dichloroethane was added freshly pulverized, fused zinc chloride (43.3 g, 0.318 mol) in one portion. The reaction mixture was heated at gentle reflux for 4.5 hours and then quenched with 700 ml of crushed ice and 500 ml of dichloromethane. The organic layer was separated and washed with water (2x 500 ml), dried over anhydrous MgSO4, filtered, and evaporated to give 92 g of an oil. This oil was purified by column chromatography (silica gel/dichloromethane) to give 33.8 g (45%) of needles, m.p. 158°-160° C.

Aufarbeitung

  1. additionwas added freshly
  2. temperatureThe reaction mixture was heated
  3. temperatureat gentle reflux for 4.5 hours
  4. customquenched with 700 ml of crushed ice and 500 ml of dichloromethane
  5. customThe organic layer was separated
  6. washwashed with water (2x 500 ml)
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3eaf12665e6c412bb52700cb9ac186b6
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04588727

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