Phosphorus oxychloride → HCID 19605166, compound

HRID 1603490Notes

Reaction equation

HRID 1603490 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([NH:13][CH2:14][C:15]1[S:16][C:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][N:19]=1)([C:8]([O:10][CH2:11][CH3:12])=[O:9])=O>>[CH2:23]([O:22][C:20]([C:17]1[S:16][C:15]2=[CH:14][N:13]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:19]2[CH:18]=1)=[O:21])[CH3:24]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 19605014HCID 19605014, compound

Product 1

HCID 19605166HCID 19605166, compoundYield 71.6%

Procedure

A 20 ml potion of phosphorus oxychloride was added to 3.53 g of 2-(ethoxalylamino)methyl-5-ethoxycarbonylthiazole under ice-cooling, and the solution was then heated under reflux for 15 hours. After cooled, the reaction solution was concentrated to dryness under reduced pressure, and 20 ml of water and 20 ml of dichloromethane were then added so as to dissolve it. Under ice-cooling, potassium carbonate was added until the solution was alkalified. The solution was extracted with dichloromethane (10 ml×4). The combined organic layer was dried over anhydrous magnesium sulfate, and then filtered, and the solvent was evaporated under reduced pressure. The resulting crude product was purified by a silica gel column chromatograph to obtain 2.37 g of 2,5-diethoxycarbonylimidazo[5,1-b]thiazole.

Workup

  1. temperaturecooling
  2. temperaturethe solution was then heated
  3. temperatureunder reflux for 15 hours
  4. temperatureAfter cooled
  5. concentrationthe reaction solution was concentrated to dryness under reduced pressure, and 20 ml of water and 20 ml of dichloromethane
  6. additionwere then added so as
  7. dissolutionto dissolve it
  8. temperatureUnder ice-cooling
  9. additionpotassium carbonate was added until the solution
  10. extractionThe solution was extracted with dichloromethane (10 ml×4)
  11. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. customthe solvent was evaporated under reduced pressure
  14. customThe resulting crude product was purified by a silica gel column chromatograph

Sources & evidence

ORD record
ord-317b2ce98f4f4ca7a33064cd0a41326f
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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