HCID 13922872, compound → HCID 13922873, compound

HRID 2232353Notes

Reaction equation

HRID 2232353 reaction equation
C([O:4][CH2:5][C:6]1[CH:18]=[CH:17][C:9]2[S:10][C:11]([S:13](=[O:16])(=[O:15])[NH2:14])=[CH:12][C:8]=2[CH:7]=1)(=O)C>[OH-].[K+].CO>[OH:4][CH2:5][C:6]1[CH:18]=[CH:17][C:9]2[S:10][C:11]([S:13](=[O:15])(=[O:16])[NH2:14])=[CH:12][C:8]=2[CH:7]=1

Participants

4

Reactant 1

HCID 13922872HCID 13922872, compound

Product 1

HCID 13922873HCID 13922873, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

A solution of 5-acetoxymethyl-2-sulfamoylbenzo[b]thiophene (5.6 g, 19.6 mmol) in 25 ml of 1M aqueous KOH and 25 ml of methanol was stirred at room temperature for 2 hours and at reflux for 21/2 hours. The mixture was filtered and the methanol was removed in vacuo. The remaining aqueous suspension was acidified with excess 6N HCl and the solid was filtered, washed with ice water and dried. The crude material (3.1 g) was chromatographed on silica gel using 5% (V/V) methanol in chloroform. Product was obtained as a yellow solid (1.85 g), m.p. 174°-176° C. Yield 41%.

Workup

  1. temperatureat reflux for 21/2 hours
  2. filtrationThe mixture was filtered
  3. customthe methanol was removed in vacuo
  4. filtrationthe solid was filtered
  5. washwashed with ice water
  6. customdried
  7. customThe crude material (3.1 g) was chromatographed on silica gel using 5% (V/V) methanol in chloroform

Sources & evidence

ORD record
ord-29f2f0d6c62e48549045253834f94c3e
Source dataset
uspto-grants-1988_11
Patent number
US04788192

Reaction notes

Loading…