Pyridine → Ethyl 4-phenyl-1,3-thiazole-2-carboxylate

HRID 868926Notes

Reaction equation

HRID 868926 reaction equation
[NH2:1][C:2](=[S:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].N1C=CC=CC=1.Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O>C(O)C>[C:19]1([C:17]2[N:1]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[S:8][CH:16]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6259Phenacyl bromideHCID 2733398Ethyl thiooxamate

Product 1

HCID 24730326Ethyl 4-phenyl-1,3-thiazole-2-carboxylateYield 75.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To ethyl 2-amino-2-thioxoacetate (4 g, 30 mmol) in ethanol (50 mL) was added pyridine (0.24 g, 3 mmol). 2-Bromo-1-phenylethanone (5 g, 25 mmol) was added after 10 minutes and the mixture was then heated at reflux for 6 hours. The resulting mixture was washed with water and extracted with EtOAc and dried over anhydrous sodium sulfate. The solution was then concentrated under vacuum to give a crude product, which was purified by column chromatography to afford the title compound as a white solid (4.4 g). MS (ESI) m/z 233 (M+H+).

Workup

  1. temperaturethe mixture was then heated
  2. temperatureat reflux for 6 hours
  3. washThe resulting mixture was washed with water
  4. extractionextracted with EtOAc
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe solution was then concentrated under vacuum
  7. customto give a crude product, which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-d5b116bca10b41a5ab760bd00d68d1a6
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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