Pyridinium chloride → Benzo[d]isothiazol-4-ol

HRID 2220329Notes

Reaction equation

C[O:2][C:3]1[C:8]2[CH:9]=[N:10][S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1>>[S:11]1[C:7]2=[CH:6][CH:5]=[CH:4][C:3]([OH:2])=[C:8]2[CH:9]=[N:10]1

Participants

Reactant 2

HCID 10176127Pyridinium chloride

HCID 193843524-Methoxybenzo[d]isothiazole

Product 1

HCID 135741992Benzo[d]isothiazol-4-olYield 32.1%

Conditions

Temperature: 150 °C

Procedure

To a sealed tube was added 4methoxy-benzo[d]isothiazole (760 mg, 4.60 mmol) and pyridine hydrochloride (5.5 g, 48 mmol). The reaction was heated to 150° C. for 18 h and was then cooled to rt. The mixture was partitioned between dichloromethane and water. The organic phase was separated and the aqueous layer was extracted with 2×30 mL dichloromethane. The combined organic phases were dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography eluting silica gel with EtOAc:hexane [0:100 to 3:7] to yield the title compound as a solid (223 mg, 32%); Mass spectrum (ion spray): m/z=151.9 (m+1).

Workup

temperaturewas then cooled to rt
customThe mixture was partitioned between dichloromethane and water
customThe organic phase was separated
extractionthe aqueous layer was extracted with 2×30 mL dichloromethane
dry with materialThe combined organic phases were dried (MgSO4)
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography
washeluting silica gel with EtOAc

Sources & evidence

ORD record: ord-43ee41e15024475096ee593ec4481c75
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417064B2

Reaction notes

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