Pyridinium chloride → HCID 20148580, compound

HRID 569073Notes

Reaction equation

HRID 569073 reaction equation
[S:1]([C:5]1[S:13][C:12]2[C:7](=[N:8][CH:9]=[C:10]([O:14]C)[CH:11]=2)[CH:6]=1)(=[O:4])(=[O:3])[NH2:2].Cl.N1C=CC=CC=1>O>[S:1]([C:5]1[S:13][C:12]2[C:7](=[N:8][CH:9]=[C:10]([OH:14])[CH:11]=2)[CH:6]=1)(=[O:3])(=[O:4])[NH2:2]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 20148565HCID 20148565, compound

Product 1

HCID 20148580HCID 20148580, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 2-sulfamoyl-6-methoxythieno[3,2-b]pyridine (512 mg, 2.1 mmol) and pyridine hydrochloride (1.62 g, 14 mmol), under a nitrogen atmosphere, was placed in an oil bath heated at 190° C. for 3/4 hour. The cooled mixture was diluted with water as the product slowly crystallized out. The mixture was extracted into ethyl acetate/methanol, washed with water, dried over anhydrous sodium sulfate, filtered through a pad of charcoal and evaporated. The residue was triturated with diethyl ether and the product was collected by filtration (330 mg, 68% yield). Crystallization from hot ethyl acetate/methanol by boiling off the methanol gave pure product, m.p. 248°-250° C.

Workup

  1. customunder a nitrogen atmosphere, was placed in an oil bath
  2. customslowly crystallized out
  3. extractionThe mixture was extracted into ethyl acetate/methanol
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered through a pad of charcoal
  7. customevaporated
  8. customThe residue was triturated with diethyl ether
  9. filtrationthe product was collected by filtration (330 mg, 68% yield)
  10. customCrystallization from hot ethyl acetate/methanol
  11. customgave pure product, m.p. 248°-250° C.

Sources & evidence

ORD record
ord-7fd1e24abeee4dfbbe08b99523b12314
Source dataset
uspto-grants-1988_03
Patent number
US04731368

Reaction notes

Loading…