Butyl iodide → HCID 178448490, Verbindung

HRID 340639

Reaktionsgleichung

Reaktionsgleichung von HRID 340639
[C:1]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].I[CH2:23][CH2:24][CH2:25][CH3:26].C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[I-].C([N+](CC)(CC)CC)C.C1(C)C=CC=CC=1>[CH2:23]([N:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[S:9]/[C:8]/1=[N:10]\[C:11](=[O:21])[C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[O:19][CH3:20])[CH2:24][CH2:25][CH3:26]

Komponenten

8

Edukt 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 87094486n-(5-Tert-butylthiazol-2-yl)-5-chloro-2-methoxybenzamide

Produkt 1

HCID 178448490HCID 178448490, VerbindungAusbeute 85,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6225Tetraethylammonium IodideKatalysatorHCID 67553Tetrabutylammonium IodideKatalysatorHCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of Example 2C (650 mg, 2 mmol), 1-iodobutane (920 mg, 5 mmol), potassium carbonate (653 mg, 4 mmol), tetrabutylammonium iodide (20 mg, 0.05 mmol), tetrabutylammonium hydrogensulfate (20 mg, 0.06 mmol) and tetraethylammonium iodide (20 mg, 0.07 mmol) in anhydrous toluene (60 mL) was refluxed for 15 h. The mixture was then washed with water, brine, dried with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was chromatographed over silica gel (EtOAc-Hexane 1:1) to afford 650 mg of the title compound. MS (DCI/NH3) m/z 381 (M+H)+.

Aufarbeitung

  1. washThe mixture was then washed with water, brine
  2. dry with materialdried with anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed over silica gel (EtOAc-Hexane 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-d3d60ed4735e4fb49b32cad7e2b5cd0a
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895592B2

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