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

HRID 1803807Notes

Reaction equation

HRID 1803807 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.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[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-sulfonamideYield 95.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 1 L round bottomed flask equipped with a magnetic stir bar, rubber septum, and argon inlet containing DCM (500 mL) was placed 6-ethoxybenzo[d]thiazole-2-sulfonamide (25 g, 108.7 mmol). To this solution at 0° C. (ice bath) was added AlCl3 (50 g, 376 mmol) portion-wise and the reaction was allowed to stir at rt for 24 h. Solvent was removed in vacuo and the residue was cautiously quenched into 3 M HCl (600 mL). The mixture was filtered and the solid was washed with cooled 3 M HCl (2×50 mL). The product was dried under high vacuum for 48 h to afford compound 1 as a yellow solid (24 g).

Workup

  1. customTo a 1 L round bottomed flask equipped with a magnetic stir bar
  2. customSolvent was removed in vacuo
  3. customthe residue was cautiously quenched into 3 M HCl (600 mL)
  4. filtrationThe mixture was filtered
  5. washthe solid was washed
  6. temperaturewith cooled 3 M HCl (2×50 mL)
  7. customThe product was dried under high vacuum for 48 h

Sources & evidence

ORD record
ord-d022544874e2455687aa94f6b832e34f
Source dataset
uspto-grants-2013_01
Patent number
US08354092B2

Reaction notes

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