Sodium Hydroxide → 2-Phenylthiazole

HRID 450102Notes

Reaction equation

HRID 450102 reaction equation
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:11][CH:12](OCC)OCC.[OH-].[Na+]>C1COCC1.O>[C:2]1([C:1]2[S:8][CH:11]=[CH:12][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 683563Thiobenzamide

Product 1

HCID 5474942-PhenylthiazoleYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of thiobenzamide (1 g, 7.3 mmol) in THF (10 ml) was added a solution of 2-bromo-1,1-diethoxy-ethane (1.4 g, 7.3 mmol) in THF (5 ml) and the reaction was heated at reflux overnight. The reaction mixture was cooled to room temperature and diluted with water (50 ml). The solution was basified with dilute sodium hydroxide and extracted with ethyl acetate: pet ether (1:4). The organic layer was then washed with water, brine and dried. Evaporation gave a residue which was purified by column chromatography over silica gel using EtOAc/pet ether as eluent to give 2-phenyl thiazole (400 mg, 34%) as solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux overnight
  3. extractionextracted with ethyl acetate: pet ether (1:4)
  4. washThe organic layer was then washed with water, brine
  5. customdried
  6. customEvaporation
  7. customgave a residue which
  8. customwas purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-e6587ebd95cb4c17a35148c257d1fdca
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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