Pyridinium chloride → 1,2-Benzisothiazol-6-ol

HRID 252147Notes

Reaction equation

HRID 252147 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][C:6]2[CH:7]=[N:8][S:9][C:5]=2[CH:4]=1.Cl.N1C=CC=CC=1>>[S:9]1[C:5]2[CH:4]=[C:3]([OH:2])[CH:11]=[CH:10][C:6]=2[CH:7]=[N:8]1

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 53743486HCID 53743486, compound

Product 1

HCID 1357420021,2-Benzisothiazol-6-olYield 83.6%

Procedure

A method similar to the method described in WO 04/043904 was used. 6-Methoxybenzo[d]isothiazole (450 mg, 2.73 mmol) and pyridine hydrochloride (3.2 g, 27.27 mmol) were heated at 210° C. in a microwave oven for 20 min. The residue was partitioned between water (30 mL) and EtOAc (3×20 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography on silica gel with EtOAc:heptane (1:1, v/v) as eluent to afford benzo[d]isothiazol-6-ol as a white solid (345 mg, 83%).

Workup

  1. customThe residue was partitioned between water (30 mL) and EtOAc (3×20 mL)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel with EtOAc:heptane (1:1

Sources & evidence

ORD record
ord-e6ca03cdf9b247cbac9b9380e30b894a
Source dataset
uspto-grants-2011_01
Patent number
US07868017B2

Reaction notes

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