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

HRID 440318Notes

Reaction equation

HRID 440318 reaction equation
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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 19096565Water ethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9e66725a1f674e719761766d3db2483f
Source dataset
uspto-grants-1996_05
Patent number
US05519040

Reaction notes

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