Pyridinium chloride → HCID 14183139, compound

HRID 845453Notes

Reaction equation

HRID 845453 reaction equation
Cl.N1C=CC=CC=1.C[O:9][C:10]1[CH:11]=[C:12]([C:16]2[N:20]=[C:19]([S:21]([NH2:24])(=[O:23])=[O:22])[S:18][N:17]=2)[CH:13]=[CH:14][CH:15]=1>>[OH:9][C:10]1[CH:11]=[C:12]([C:16]2[N:20]=[C:19]([S:21]([NH2:24])(=[O:23])=[O:22])[S:18][N:17]=2)[CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 14183135HCID 14183135, compound

Product 1

HCID 14183139HCID 14183139, compound

Procedure

Pyridine hydrochloride (160 g) was preheated to 205° and 8 g of finely ground 3-(3-methoxyphenyl)-1,2,4-thiadiazole-5-sulfonamide was added. Said temperature was maintained for 15 minutes. The mixture was then poured into ice water (1000 ml) and extracted with ethyl acetate (3×500 ml), and the extracts were washed with saturated sodium chloride solution (500 ml) and dried over anhydrous magnesium sulfate. Concentration gave 5.3 g of product. Flash chromatography using 10% ethyl acetate/dichloromethane as an eluent gave 2.3 g of product. This was combined with 0.7 g of product from a previous reaction and recrystallized in hot water to give 2.2 g of solid, m.p. 191°-192°.

Workup

  1. customwas preheated to 205°
  2. temperaturewas maintained for 15 minutes
  3. extractionextracted with ethyl acetate (3×500 ml)
  4. washthe extracts were washed with saturated sodium chloride solution (500 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationConcentration

Sources & evidence

ORD record
ord-a54d89280c8a447294e8a9a461bc924d
Source dataset
uspto-grants-1988_07
Patent number
US04758578

Reaction notes

Loading…