Sodium Hydroxide → benzo[d]isothiazole-5-carboxylic acid

HRID 1880430Notes

Reaction equation

HRID 1880430 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([O:12]C)=[O:11])=[CH:9][C:4]=2[CH:3]=[N:2]1.[OH-].[Na+]>CO>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:4]=2[CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66920624Methyl 1,2-benzisothiazole-5-carboxylate

Product 1

HCID 58123091benzo[d]isothiazole-5-carboxylic acidYield 84.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

61 mg of methyl benzo[d]isothiazole-5-carboxylate was dissolved in 1.26 mL methanol and treated with 1.26 mL 10% aqueous sodium hydroxide. The mixture was stirred 18 h at room temperature. The reaction mixture was concentrated, and then diluted with water. Acidified to pH ˜3 and collected the precipitate by filtration. The filtercake was washed with water. The solid was then dried under high vacuum to yield 48 mg of benzo[d]isothiazole-5-carboxylic acid as a white solid. 1H NMR (400 MHz, DMSO-d6) δδ ppm 8.08 (dd, J=8.49, 1.46 Hz, 1 H) 8.31 (d, J=8.58 Hz, 1 H) 8.79 (s, 1 H) 9.24 (d, J=0.78 Hz, 1 H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. customAcidified to pH ˜3 and collected the precipitate
  4. filtrationby filtration
  5. washThe filtercake was washed with water
  6. customThe solid was then dried under high vacuum

Sources & evidence

ORD record
ord-35524680a5ee4377a34d31226504f003
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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