Hydrochloric Acid → 4,6-Dimethylbenzo[d]isothiazole-3-carboxylic acid

HRID 388463Notes

Reaction equation

HRID 388463 reaction equation
[CH3:1][C:2]1[C:7]2[C:8]([C:11](N)=[O:12])=[N:9][S:10][C:6]=2[CH:5]=[C:4]([CH3:14])[CH:3]=1.[OH-:15].[K+].Cl>CCO.O>[CH3:1][C:2]1[C:7]2[C:8]([C:11]([OH:15])=[O:12])=[N:9][S:10][C:6]=2[CH:5]=[C:4]([CH3:14])[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 584974364,6-Dimethyl-1,2-benzisothiazole-3-carboxylic acid amide

Product 1

HCID 584973864,6-Dimethylbenzo[d]isothiazole-3-carboxylic acidYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 4,6-dimethyl-1,2-benzisothiazole-3-carboxylic acid amide (20 mg, 0.097 mmol) in EtOH (10 mL) and H2O (2 mL) is added KOH (11′mg, 0.19 mmol). The solution is heated to 85° C. for 48 hours. The solution is cooled down and is placed in an ice bath. Conc. HCl is added to adjust the pH of the solution to 2. The precipitated solid is collected by means of filtration to afford 4,6-Dimethyl-1,2-benzisothiazole-3-carboxylic acid (15 mg, 75%).

Workup

  1. temperatureThe solution is cooled down
  2. customis placed in an ice bath
  3. filtrationThe precipitated solid is collected by means of filtration

Sources & evidence

ORD record
ord-571a284335fc43bc8eb820b22c57a297
Source dataset
uspto-grants-2013_02
Patent number
US08377949B2

Reaction notes

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