Sodium Carbonate → 2-(2-Thienyl)thiazole

HRID 1625913Notes

Reaction equation

HRID 1625913 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[S:7]1[CH:11]=[CH:10][CH:9]=[C:8]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(OCC)(=O)C>[S:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:2]1[S:3][CH:4]=[CH:5][N:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 764302-BromothiazoleHCID 27339602-Thiopheneboronic acid

Product 1

HCID 5475102-(2-Thienyl)thiazoleYield 64.5%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromothiazole (15.0 g) and 2-thiopheneboronic acid (14.0 g) were dissolved in dimethoxyethane (150 ml). To the mixture was added bis(triphenyl)phosphine palladium(II)dichloride (3.2 g) and 2M sodium carbonate (137 ml), and the mixture was refluxed under argon atmosphere for 2 hours. The mixture was cooled to room temperature, and the reaction solution was diluted with ethyl acetate, and washed with water. The organic layer was collected, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=96:4) to give 2-(2-thienyl)thiazole (9.87 g) as oil. APCI-Mass m/z 168 (M+H)

Workup

  1. temperaturethe mixture was refluxed under argon atmosphere for 2 hours
  2. washwashed with water
  3. customThe organic layer was collected
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=96:4)

Sources & evidence

ORD record
ord-02ac42cd92ec4fcdba6c346cd1381a01
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

Loading…