Potassium Cyanide → 4-hydroxy-1H-1,2-benzisothiazole-1,1,3(2H)-trione

HRID 1995387Notes

Reaction equation

HRID 1995387 reaction equation
NC1C2C(OC)=CC=CC=2S(=O)(=O)N=1.[OH-].[Na+].C[O:18][C:19]1[C:24]2[C:25](=[O:30])[NH:26][S:27](=[O:29])(=[O:28])[C:23]=2[CH:22]=[CH:21][CH:20]=1.[C-]#N.[K+].[K]>CS(C)=O>[OH:18][C:19]1[C:24]2[C:25](=[O:30])[NH:26][S:27](=[O:29])(=[O:28])[C:23]=2[CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 5

HCID 9032Potassium CyanideHCID 14798Sodium HydroxideHCID 5462222PotassiumHCID 149840514-Methoxy-1H-1lambda~6~,2-benzothiazole-1,1,3(2H)-trioneHCID 155671643-Amino-4-methoxy-1,2-benzoisothiazole-1,1-dioxide

Product 1

HCID 14865224-hydroxy-1H-1,2-benzisothiazole-1,1,3(2H)-trioneYield 62%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.5 gm (11.8 mmols) of 3-amino-4-methoxy-1,2-benzoisothiazole-1,1-dioxide were reacted with sodium hydroxide analogous to Example 5, and by subsequent acidification the reaction product was converted into 4-methoxy-1,2-benzoisothiazol-3(2H)-one-1,1-dioxide. The obtained compound, together with 650 mg (10 mmols) of potassium cyanide in dimethyl-sulfoxide, was heated at 180° C. for 3 hours. After addition of petroleum ether the potassium salt of the product was precipitated, and the precipitate was dissolved in water. After acidifying with aqueous hydrochloric acid, filtering and recrystallizing, 1.46 gm (62% of theory) of 4-hydroxy-1,2-benzoisothiazol-3(2H)-one-1,1-dioxide were obtained.

Workup

  1. customwas precipitated
  2. dissolutionthe precipitate was dissolved in water
  3. filtrationfiltering
  4. customrecrystallizing

Sources & evidence

ORD record
ord-9028caa34a404d9e8ab189188776807c
Source dataset
uspto-grants-1983_09
Patent number
US04404230

Reaction notes

Loading…