Potassium Carbonate → N-t-butyl-5-phenyl-2-thiazole sulfonamide

HRID 440318Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 440318
Br[C:2]1[S:6][C:5]([S:7]([NH:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:9])=[O:8])=[N:4][CH:3]=1.[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.C(O)C.C(OCC)(=O)C>[C:11]([NH:10][S:7]([C:5]1[S:6][C:2]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:3][N:4]=1)(=[O:9])=[O:8])([CH3:14])([CH3:13])[CH3:12]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 67055896HCID 67055896, Verbindung

Produkt 1

HCID 22406990N-t-butyl-5-phenyl-2-thiazole sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

In 10 mL of deoxygenated toluene was added 5-bromo-2-N-t-butylthiazole sulfonamide (0.30 g, 1.0 mmol), phenylboronic acid (0.12 g, 1.0 mmol) and potassium carbonate (0.28 g, 2.0 mmol) in 1.5 mL of water/ethanol (2:1). The mixture was deoxygenated for 30 min.. Tetrakis(triphenylphosphine) palladium (O) was added and reaction heated at reflux for 36 h. The reaction was diluted with ethyl acetate and washed with water (2X) followed by brine. The solvent was removed under reduced pressure and the product subjected to flash chromatography (3:1 hexane/ethyl acetate) to afford N-t-butyl-5-phenyl-2-thiazole sulfonamide.

Aufarbeitung

  1. customThe mixture was deoxygenated for 30 min.
  2. additionTetrakis(triphenylphosphine) palladium (O) was added
  3. customreaction
  4. temperatureheated
  5. temperatureat reflux for 36 h
  6. washwashed with water (2X)
  7. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9e66725a1f674e719761766d3db2483f
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05519040

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