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

HRID 345776Notes

Reaction equation

HRID 345776 reaction equation
B(Br)(Br)Br.C([O:7][C:8]1[CH:20]=[CH:19][C:11]2[N:12]=[C:13]([S:15]([NH2:18])(=[O:17])=[O:16])[S:14][C:10]=2[CH:9]=1)C>C(Cl)Cl>[OH:7][C:8]1[CH:20]=[CH:19][C:11]2[N:12]=[C:13]([S:15]([NH2:18])(=[O:17])=[O:16])[S:14][C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 3295EthoxzolamideHCID 25134Boron tribromide

Product 1

HCID 68521296-Hydroxy-1,3-benzothiazole-2-sulfonamideYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1 M solution of BBr3 in CH2Cl2 (23 mL, 0.022 mol) was cooled to -80° C. in a dry ice/acetone bath under a N2 atmosphere. A suspension of 6-ethoxy-2-benzothiazolesulfonamide (0.5 g, 0.002 mol) in 75 mL of CH2Cl2 was added slowly to the cooled BBR3 solution The reaction was removed from the cooling bath and stirred at room temperature for 15 hours. It was poured into ice-water, stirred for 30 min, and filtered to Yield 0.35 g of product (73.8%). The product was purified by recrystallization from MeOH/H2O; mp 209°-212° C.; M/S m/e 230 (M,calcd 230).

Workup

  1. additionwas added slowly to the cooled BBR3 solution The reaction
  2. customwas removed from the cooling bath
  3. additionIt was poured into ice-water
  4. stirringstirred for 30 min
  5. filtrationfiltered

Sources & evidence

ORD record
ord-5bb0097cdfb74a4fbf6fd27b901fbef5
Source dataset
uspto-grants-1991_10
Patent number
US05059613

Reaction notes

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