Formic Acid → Thiazolo[4,5-c]pyridine

HRID 352874Notes

Reaction equation

HRID 352874 reaction equation
C(O[NH:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[SH:13])(C)(C)C.[CH:14](O)=O>>[S:13]1[C:12]2[CH:11]=[CH:10][N:9]=[CH:8][C:7]=2[N:6]=[CH:14]1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 178454482HCID 178454482, compound

Product 1

HCID 585837Thiazolo[4,5-c]pyridine

Procedure

In formic acid (60 ml) was dissolved 3-(tert-butoxyamino)-4-mercaptopyridine (9.20 g), followed by heating under reflux for 4 hours. After the reaction mixture was concentrated under reduced pressure and a 5N aqueous solution (100 ml) of potassium hydroxide was added to the residue, the resulting mixture was extracted with ether. The organic layer was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. Diethyl ether was added to the residue and the solid so precipitated was collected by filtration, whereby the title compound was obtained as a colorless solid (3.97 g).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 4 hours
  3. concentrationAfter the reaction mixture was concentrated under reduced pressure
  4. additiona 5N aqueous solution (100 ml) of potassium hydroxide was added to the residue
  5. extractionthe resulting mixture was extracted with ether
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent
  9. additionDiethyl ether was added to the residue
  10. customthe solid so precipitated
  11. filtrationwas collected by filtration, whereby the title compound

Sources & evidence

ORD record
ord-e17dd22dd2df42c9866bef3f0b837b1e
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

Loading…