Pyridinium chloride → HCID 135603722, compound

HRID 845454Notes

Reaction equation

HRID 845454 reaction equation
Cl.N1C=CC=CC=1.C[O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]=[C:19]([S:21]([NH2:24])(=[O:23])=[O:22])[S:18][N:17]=2)=[CH:12][CH:11]=1>>[OH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]=[C:19]([S:21]([NH2:24])(=[O:23])=[O:22])[S:18][N:17]=2)=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 14183094HCID 14183094, compound

Product 1

HCID 135603722HCID 135603722, compoundYield 7.5%

Procedure

To 35 g of pyridine hydrochloride at 200° was added 28 g of 3-(4-methoxyphenyl)-1,2,4-thiadiazole-5-sulfonamide with stirring. The resulting mixture was maintained at 200°-4° for 10 minutes, cooled slightly, poured into excess ice water and extracted with ethyl acetate (3x). The organics were dried over anhydrous magnesium sulfate and concentrated to give 2.0 g of solid. Flash chromatography using 10% ethyl acetate/dichloromethane as eluent gave 1.0 g of solid. This was combined with 0.5 g of the same compound from a previous reaction and recrystallized from water using decolorizing carbon to give 0.95 g of solid, m.p. 219°-221°.

Workup

  1. temperatureThe resulting mixture was maintained at 200°-4° for 10 minutes
  2. temperaturecooled slightly
  3. extractionextracted with ethyl acetate (3x)
  4. dry with materialThe organics were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-33de00c8ff2f4c4d89b1e30adf58cf18
Source dataset
uspto-grants-1988_07
Patent number
US04758578

Reaction notes

Loading…