Phosphorus oxychloride → 3-Allyloxycarbonylaminoimidazo[5,1-b]thiazole

HRID 1603466Notes

Reaction equation

HRID 1603466 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([O:9][C:10]([NH:12][C:13]1[N:14]=[C:15]([CH2:18][NH:19][CH:20]=O)[S:16][CH:17]=1)=[O:11])[CH:7]=[CH2:8]>C1(C)C=CC=CC=1>[CH2:6]([O:9][C:10]([NH:12][C:13]1[N:14]2[CH:20]=[N:19][CH:18]=[C:15]2[S:16][CH:17]=1)=[O:11])[CH:7]=[CH2:8]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 196051274-Allyloxycarbonylamino-2-(formylamino)methylthiazole

Product 1

HCID 196050383-Allyloxycarbonylaminoimidazo[5,1-b]thiazoleYield 75.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A 6.4 ml portion of phosphorus oxychloride was added to a suspension obtained by adding 17 ml of dry toluene to 3.408 g of 4-allyloxycarbonylamino-2-(formylamino)methylthiazole, and the mixture was then stirred at an oil temperature of 100° C. for 45 minutes. The solvent was evaporated under reduced pressure, and to the resulting residue, 200 ml of dichloromethane and 100 ml of 0.1N sodium hydroxide were added. The solution was adjusted to pH 8.0 with a 2N aqueous sodium hydroxide solution under stirring. After the removal of insolubles by filtration, the organic layer was separated from the filtrate, and it was combined with a liquid extracted from the aqueous layer with 100 ml of dichloromethane, dried (magnesium sulfate), and then filtered. Further, the solvent was evaporated under reduced pressure to obtain an ocherous powder, and this powder was then purified by a silica gel column chromatograph to obtain 2.390 g of the title compound as a light orange powder.

Workup

  1. customobtained
  2. customThe solvent was evaporated under reduced pressure
  3. additionto the resulting residue, 200 ml of dichloromethane and 100 ml of 0.1N sodium hydroxide were added
  4. stirringunder stirring
  5. customAfter the removal of insolubles
  6. filtrationby filtration
  7. customthe organic layer was separated from the filtrate, and it
  8. extractionextracted from the aqueous layer with 100 ml of dichloromethane
  9. dry with materialdried (magnesium sulfate)
  10. filtrationfiltered
  11. customFurther, the solvent was evaporated under reduced pressure
  12. customto obtain an ocherous powder
  13. customthis powder was then purified by a silica gel column chromatograph

Sources & evidence

ORD record
ord-1513484d1bb0418caa289be3736891ba
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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