Pyridinium chloride → HCID 13922842, compound

HRID 2232340Notes

Reaction equation

HRID 2232340 reaction equation
Cl.N1C=CC=CC=1.C[O:9][C:10]1[CH:22]=[CH:21][C:13]2[S:14][C:15]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:16][C:12]=2[CH:11]=1>>[OH:9][C:10]1[CH:22]=[CH:21][C:13]2[S:14][C:15]([S:17](=[O:19])(=[O:20])[NH2:18])=[CH:16][C:12]=2[CH:11]=1

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 13922841HCID 13922841, compound

Product 1

HCID 13922842HCID 13922842, compoundYield 65%

Conditions

Temperature
190 °C

Procedure

Pyridine hydrochloride (50 g) was heated to 190° C. and to the melt was added 5-methoxy-2-sulfamoylbenzo[b]thiophene (12.78 g, 0.053 m). The mixture was stirred at 190° C. for 2 hours and then poured into ice and extracted with ethyl acetate (3×200 ml). The combined extract was washed with 3N HCl, dried over Na2SO4 and filtered through a pad of filter aid and charcoal. The filtrate was concentrated under reduced pressure and the residue was crystallized from nitromethane to yield 7.83 g (64%) of product melting at 197°-198.5° C. An analytical sample melted at 192.5°-193.5° C. after recrystallization from nitromethane and treatment with decolorizing carbon.

Workup

  1. additionpoured into ice
  2. extractionextracted with ethyl acetate (3×200 ml)
  3. extractionThe combined extract
  4. washwas washed with 3N HCl
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered through a pad of filter aid and charcoal
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was crystallized from nitromethane

Sources & evidence

ORD record
ord-639ab00080fe498aa329c8ea4d706d97
Source dataset
uspto-grants-1988_11
Patent number
US04788192

Reaction notes

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