Allyl Alcohol → 3-(Allyloxycarbonyl)methylimidazo[5,1-b]thiazole

HRID 1603492Notes

Reaction equation

HRID 1603492 reaction equation
[O-]CC.[Na+].[CH2:5]([OH:8])[CH:6]=[CH2:7].C([O:11][C:12]([CH2:14][C:15]1[N:16]2[CH:22]=[N:21][CH:20]=[C:17]2[S:18][CH:19]=1)=O)C>>[CH2:5]([O:8][C:12]([CH2:14][C:15]1[N:16]2[CH:22]=[N:21][CH:20]=[C:17]2[S:18][CH:19]=1)=[O:11])[CH:6]=[CH2:7]

Participants

4

Reactant 3

HCID 7858Allyl AlcoholHCID 2723922Sodium ethoxideHCID 196050653-Ethoxycarbonylmethylimidazo[5,1-b]thiazole

Product 1

HCID 196050123-(Allyloxycarbonyl)methylimidazo[5,1-b]thiazole

Procedure

A 30 mg potion of a sodium ethoxide powder was added to 6.2 ml of an allyl alcohol solution containing 314.2 mg of 3-ethoxycarbonylmethylimidazo[5,1-b]thiazole, and the mixture was then was then heated under reflux for 7 hours. After cooled, the reaction solution was concentrated under reduced pressure, and the organic layer extracted with dichloromethane (10 ml×4) 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 240.4 mg of the title compound as a colorless solid.

Workup

  1. temperaturethe mixture was then was then heated
  2. temperatureunder reflux for 7 hours
  3. temperatureAfter cooled
  4. concentrationthe reaction solution was concentrated under reduced pressure
  5. extractionthe organic layer extracted with dichloromethane (10 ml×4)
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customThe resulting crude product was purified by a silica gel column chromatograph

Sources & evidence

ORD record
ord-bcc09a9dffdc4d64a4f4c2988d62cb07
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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