1-(Methylsulphonyl)acetone → 3-Methanesulfonyl-2-methyl-4-phenyl-6-trifluoromethoxy-quinoline

HRID 13654

Reaktionsgleichung

Reaktionsgleichung von HRID 13654
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O.[CH3:21][S:22]([CH2:25][C:26](=O)[CH3:27])(=[O:24])=[O:23]>CC(O)C.O.O.[Na+].Cl[Au-](Cl)(Cl)Cl>[CH3:21][S:22]([C:25]1[C:26]([CH3:27])=[N:1][C:2]2[C:3]([C:13]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:4][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:6][CH:7]=2)(=[O:24])=[O:23]

Komponenten

5

Edukt 2

HCID 786951-(Methylsulphonyl)acetoneHCID 767339(2-Amino-5-trifluoromethoxy-phenyl)-phenyl-methanone

Produkt 1

HCID 120016253-Methanesulfonyl-2-methyl-4-phenyl-6-trifluoromethoxy-quinolineAusbeute 40,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 18949434Sodium tetrachloroaurate dihydrateKatalysatorHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

(2-Amino-5-trifluoromethoxy-phenyl)-phenyl-methanone (0.3 g, 1 mmol), methylsulfonylacetone (0.22 g, 2 mmol) and sodium tetrachloroaurate (III) dihydrate (13 mg, 0.036 mmol) were mixed in 2-propanol (3 mL) and heated at reflux under nitrogen for 5 days. 2-propanol was evaporated and the residue was purified by flash chromatography on silica gel in heptane/ethyl acetate 2:1. One obtained 154 mg (34%) of a white solid. MS: m/z=382 (M+H).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux under nitrogen for 5 days
  3. custom2-propanol was evaporated
  4. customthe residue was purified by flash chromatography on silica gel in heptane/ethyl acetate 2:1

Quellen und Nachweise

ORD-Eintrag
ord-5070543b4c8f42a98c06b14f1070abda
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728142B2

Verknüpfte Notizen

Wird geladen…