Ethoxzolamide → 6-Hydroxy-1,3-benzothiazole-2-sulfonamide

HRID 2417787Notes

Reaction equation

HRID 2417787 reaction equation
C([O:3][C:4]1[CH:16]=[CH:15][C:7]2[N:8]=[C:9]([S:11]([NH2:14])(=[O:13])=[O:12])[S:10][C:6]=2[CH:5]=1)C.[Cl-].[Al+3].[Cl-].[Cl-]>CCCCCCC>[OH:3][C:4]1[CH:16]=[CH:15][C:7]2[N:8]=[C:9]([S:11]([NH2:14])(=[O:13])=[O:12])[S:10][C:6]=2[CH:5]=1

Participants

4

Reactant 2

HCID 3295EthoxzolamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 68521296-Hydroxy-1,3-benzothiazole-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

A stirred mixture of 6-ethoxy-2-benzothiazolesulfonamide (20g.) and aluminum chloride (40 g.) in heptane (500 ml) was heated at reflux for 4 hours and cooled. The heptane was decanted from the reaction mixture which was then treated with ice water (500 ml.). After 1/2 hour the crude product was filtered, dissolved in warm dilute sodium hydroxide, filtered and acidified with concentrated hydrochloric acid to give 7.5 g. of 6-hydroxy-2-benzothiazolesulfonamide which melts at 225°-228° C. after recrystallization from acetic acid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperaturecooled
  4. customThe heptane was decanted from the reaction mixture which
  5. additionwas then treated with ice water (500 ml.)
  6. filtrationAfter 1/2 hour the crude product was filtered
  7. dissolutiondissolved
  8. temperaturein warm dilute sodium hydroxide
  9. filtrationfiltered
  10. customto give 7.5 g
  11. customof 6-hydroxy-2-benzothiazolesulfonamide which melts at 225°-228° C. after recrystallization from acetic acid

Sources & evidence

ORD record
ord-89058bb65cf2441ebef4e4a268f3d94a
Source dataset
uspto-grants-1984_09
Patent number
US04470991

Reaction notes

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