Potassium Carbonate → 6-Chloro-1,2-benzothiazole-3-carboxylic acid

HRID 424650Notes

Reaction equation

[Mn]([O-])(=O)(=O)=O.[K+].[Cl:7][C:8]1[CH:18]=[CH:17][C:11]2[C:12]([CH2:15][OH:16])=[N:13][S:14][C:10]=2[CH:9]=1.C(=O)([O-])[O-:20].[K+].[K+]>O>[Cl:7][C:8]1[CH:18]=[CH:17][C:11]2[C:12]([C:15]([OH:20])=[O:16])=[N:13][S:14][C:10]=2[CH:9]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Potassium permanganate (1.69 mmol) was added in several batches a solution of (6-chlorobenzo[d]isothiazol-3-yl)methanol (2.50 mmol) in water (3 mL). Potassium carbonate (2.90 mmol) was added and the reaction mixture was maintained for 30 min at 25° C. The insoluble materials were removed by filtration and the aqueous layer was extracted with ethyl acetate (3×10 mL). The pH of the aqueous layer was adjusted to 3-4 by the addition of 1 N hydrochloric acid and the reaction mixture was maintained for 10 min. The solids were collected by filtration to provide 6-chlorobenzo[d]isothiazole-3-carboxylic acid in 15% yield as a white solid.

Workup

customThe insoluble materials were removed by filtration
extractionthe aqueous layer was extracted with ethyl acetate (3×10 mL)
additionThe pH of the aqueous layer was adjusted to 3-4 by the addition of 1 N hydrochloric acid
temperaturethe reaction mixture was maintained for 10 min
filtrationThe solids were collected by filtration

Sources & evidence

ORD record: ord-56cab39ac54d463d948fdf52632f9ae2
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106066B2

Reaction notes

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