Cesium carbonate → Methyl 2-chloro-4-(4-(2-dimethylaminoethyl)phenoxy)-5-methylsulfonylbenzoate

HRID 1106502

Reaktionsgleichung

Reaktionsgleichung von HRID 1106502
[Cl:1][C:2]1[CH:11]=[C:10](F)[C:9]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:17][N:18]([CH3:28])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+].C([O-])(O)=O.[Na+]>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:11]=[C:10]([O:27][C:24]2[CH:23]=[CH:22][C:21]([CH2:20][CH2:19][N:18]([CH3:17])[CH3:28])=[CH:26][CH:25]=2)[C:9]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 68313HordenineHCID 516892Sodium BicarbonateHCID 10611840Methyl 2-chloro-4-fluoro-5-methylsulfonylbenzoate

Produkt 1

HCID 18788900Methyl 2-chloro-4-(4-(2-dimethylaminoethyl)phenoxy)-5-methylsulfonylbenzoateAusbeute 29,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

534 mg of methyl 2-chloro-4-fluoro-5-methylsulfonylbenzoate, 331 mg of 4-(2-dimethylaminoethyl)phenol and 2.0 g of Cs2CO3 were dissolved in 10 ml of NMP and the mixture was stirred at 100° C. for 3 hours. The reaction mixture was poured onto 150 ml of a saturated aqueous NaHCO3 solution and extracted 3 times using 100 ml of EA each time. The organic phase was dried over Na2SO4 and the solvent was removed in vacuo. Chromatography on silica gel using EA/MeOH 3:1 yields 240 mg of a viscous oil.

Aufarbeitung

  1. extractionextracted 3 times
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3918a93898e143f69244c804ea6d1915
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06057322

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