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

HRID 1110376Notes

Reaction equation

HRID 1110376 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>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

3

Reactant 1

HCID 3295Ethoxzolamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 1 M solution of BBR in MCH2C12 (23 ml., 0.022 mol) was cooled to -80° C. in a dry ice/acetone bath stirred for 20 minutes. (The reaction was accomplished under a nitrogen atmosphere.) A suspension of 6-ethoxy-2-benzothiazolesulfonamide (0.5g., 0.002 mol) in 75 ml of CH2Cl2 was added slowly to the coole bath and stirred at room temperature overnight. The reaction was poured into ice water and filtered to yield 0.35 g of product (73.8% yield). The product was purified by recrystallization from methanol and water. m.p. 209° C.; NMR(DMSO-D6), δ8.4 (s, lH), 8.3-7.0 (m, 3H), 3.5 (s, 2H); DMSO-D6 /D2O)6 δ8.3-7.0 (m, 3H), 4.2 (s, 2H).

Workup

  1. additionwas added slowly to the coole bath
  2. stirringstirred at room temperature overnight
  3. filtrationfiltered

Sources & evidence

ORD record
ord-685f16308810445386b72623daa2b6a8
Source dataset
uspto-grants-1990_12
Patent number
US04975449

Reaction notes

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