Hydrochloric Acid → HCID 67781003, compound

HRID 2209444Notes

Reaction equation

HRID 2209444 reaction equation
C(S)C.[Cl-].[Al+3].[Cl-].[Cl-].[CH:8]([C:11]1[C:16]2[C:17](=[O:32])[N:18]([C:22]3[C:27]([F:28])=[C:26]([F:29])[N:25]=[C:24]([F:30])[C:23]=3[F:31])[S:19](=[O:21])(=[O:20])[C:15]=2[CH:14]=[C:13]([O:33]C)[CH:12]=1)([CH3:10])[CH3:9].Cl>C(Cl)(Cl)Cl>[CH:8]([C:11]1[C:16]2[CH2:17][N:18]([C:22]3[C:27]([F:28])=[C:26]([F:29])[N:25]=[C:24]([F:30])[C:23]=3[F:31])[S:19][C:15]=2[CH:14]=[C:13]([OH:33])[CH:12]=1)([CH3:10])[CH3:9].[S:19]1(=[O:20])(=[O:21])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:16]=2[C:17](=[O:32])[NH:18]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 15291067HCID 15291067, compound

Product 1

HCID 67781003HCID 67781003, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Ethanethiol (0.82 ml, 11.26 mmol) was added to a suspension of aluminium chloride (0.99 g, 7.42 mmol) in chloroform (20 ml) at 0° C. The mixture was stirred for 10 minutes then a solution of 4-isopropyl-6-methoxy 2-(2,3,5,6-tetrafluoro-4-pyridyl) 1,2-benzisothiazol-3(2H)-one 1,1-dioxide (0.5 g, 1.73 mmol) in chloroform (10 ml) was added. The mixture was stirred at room temperature for 2-3 hours, then at reflux for 48 hours. The mixture was then cooled, poured over ice-water, acidified with dilute hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with water, then brine, and then was dried over sodium sulfate. The solvent was removed in vacuo and the residue was purified by column chromatography on silica eluting with 40% ethyl acetate/hexane to afford 0.3 g (62%) of 4-isopropyl-6-hydroxy-2-(2,3,5,6-tetrafluoro-4-pyridyl)-1,2-benzisothiazol-1,2-benzisothiazol-3(2H)-one 1,1-dioxide, m.p. 164.5°-165.5° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 2-3 hours
  2. temperatureat reflux for 48 hours
  3. temperatureThe mixture was then cooled
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialbrine, and then was dried over sodium sulfate
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by column chromatography on silica eluting with 40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-9dec4684f3a942c49c6139978af0c05c
Source dataset
uspto-grants-1995_10
Patent number
US05455255

Reaction notes

Loading…