Dimethyl-p-toluidine → 4-Chloro-6-iodo-3-methanesulfonyl-2-methyl-quinoline

HRID 13653

Reaktionsgleichung

Reaktionsgleichung von HRID 13653
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([S:13]([CH3:16])(=[O:15])=[O:14])=[C:5]2O.CN(C)C1C=CC(C)=CC=1.P(Cl)(Cl)([Cl:30])=O>C1(C)C=CC=CC=1>[Cl:30][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([I:1])[CH:3]=2)[N:8]=[C:7]([CH3:12])[C:6]=1[S:13]([CH3:16])(=[O:15])=[O:14]

Komponenten

5

Edukt 3

HCID 7471Dimethyl-p-toluidineHCID 24813Phosphorus oxychlorideHCID 178432192HCID 178432192, Verbindung

Produkt 1

HCID 120016244-Chloro-6-iodo-3-methanesulfonyl-2-methyl-quinolineAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

6-Iodo-3-methanesulfonyl-2-methyl-quinolin-4-ol (example C.2) (14.7 g, 40.5 mmol) and N,N-dimethyl-p-toluidine (11.7 mL, 81 mmol) were dissolved in toluene (150 mL) and heated under argon to reflux. Then phosphorous oxychloride (4.1 mL, 44.5 mmol) was added and heating at reflux continued for 9.5 h. The thick suspension became gradually a dark solution. The reaction mixture was allowed to cool and then extracted with dichloromethane (not soluble in toluene), cold 1 N HCl (2×), and sat. NaCl (2×). The product was crystallized from heptane/dichloromethane. One obtained 12 g (78%) of white crystals. MS: m/z=381 (M).

Aufarbeitung

  1. temperatureheated under argon
  2. temperatureto reflux
  3. temperatureheating
  4. temperatureat reflux
  5. temperatureto cool
  6. extractionextracted with dichloromethane (not soluble in toluene), cold 1 N HCl (2×), and sat. NaCl (2×)
  7. customThe product was crystallized from heptane/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-02a1067405be4f21a8572dc3c61a0744
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728142B2

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