Selenium Dioxide → Ethyl 2-(2-propanesulfonylamino-1,3-thiazol-4-yl)glyoxylate

HRID 325369Notes

Reaction equation

HRID 325369 reaction equation
[Se](=O)=O.[O:4]1CCOCC1.[CH2:10]([S:13]([NH:16][C:17]1[S:18][CH:19]=[C:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:21]=1)(=[O:15])=[O:14])[CH2:11][CH3:12]>O>[CH2:10]([S:13]([NH:16][C:17]1[S:18][CH:19]=[C:20]([C:22](=[O:4])[C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:21]=1)(=[O:15])=[O:14])[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 24007Selenium Dioxide3×HCID 312751,4-DioxaneHCID 20254391Ethyl 2-(2-propanesulfonylamino-1,3-thiazol-4-yl)acetate

Product 1

HCID 20254346Ethyl 2-(2-propanesulfonylamino-1,3-thiazol-4-yl)glyoxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution prepared by stirring a mixture of selenium dioxide (6.2 g.), dioxane (320 ml.) and water (6.4 ml.) at 50° to 60° C. was added ethyl 2-(2-propanesulfonylamino-1,3-thiazol-4-yl)acetate, which can be represented as ethyl 2-(2-propanesulfonylimino-2,3-dihydro-1,3-thiazol-4-yl)acetate, (16.3 g.), and the mixture was refluxed for 1 hour. To the mixture was added selenium dioxide (0.6 g.), and the mixture was further refluxed for 30 minutes and selenium dioxide (0.3 g.) was added thereto, and then the mixture was further refluxed for 30 minutes. After the reaction, the reaction mixture was filtered, and then dioxane was distilled off. The residue was dissolved in ethyl acetate under heating and then treated with activated charcoal. The solvent was distilled off, and the residue was washed with a small amount of ethyl acetate and diethyl ether in turn and dried to give ethyl 2-(2-propanesulfonylamino-1,3-thiazol-4-yl)glyoxylate, which can be represented as ethyl 2-(2-propanesulfonylimino-2,3-dihydro-1,3-thiazol-4-yl)glyoxylate, (12.5 g.), mp 132° to 134° C.

Workup

  1. customTo a solution prepared
  2. temperaturethe mixture was refluxed for 1 hour
  3. temperaturethe mixture was further refluxed for 30 minutes
  4. temperaturethe mixture was further refluxed for 30 minutes
  5. customAfter the reaction
  6. filtrationthe reaction mixture was filtered
  7. distillationdioxane was distilled off
  8. dissolutionThe residue was dissolved in ethyl acetate
  9. temperatureunder heating
  10. additiontreated with activated charcoal
  11. distillationThe solvent was distilled off
  12. washthe residue was washed with a small amount of ethyl acetate and diethyl ether in turn
  13. customdried

Sources & evidence

ORD record
ord-6d2cb5c617ef4fafba73a7190153a592
Source dataset
uspto-grants-1984_04
Patent number
US04440766

Reaction notes

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