Sodium Hydroxide → 1,2-Benzisothiazole-3-carboxylic acid

HRID 2064766Notes

Reaction equation

HRID 2064766 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10](N)=[O:11])=[N:2]1.[OH-:13].[Na+]>CO>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]([OH:11])=[O:13])=[N:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 156394701,2-Benzothiazole-3-carboxamide

Product 1

HCID 945121,2-Benzisothiazole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of benzo[d]isothiazole-3-carboxylic acid amide (5.05 mmol) in MeOH (100 mL) is treated with an aqueous NaOH solution (10 M, 10.0 mL) and heated to reflux for 16 h. The mixture is cooled to RT, concentrated in vacuo, made acidic by addition of hydrochloric acid (pH<2) and kept for 2 h at 0° C. The obtained precipitate is filtered off and dried in vacuo to give the desired product which is used without further purification. LC-MS: tR=0.73 min; [M+H]+=180.0.

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 h
  3. concentrationconcentrated in vacuo
  4. additionmade acidic by addition of hydrochloric acid (pH<2)
  5. filtrationThe obtained precipitate is filtered off
  6. customdried in vacuo

Sources & evidence

ORD record
ord-f5c05bacb99848caa0e7404abb3d54bf
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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