Methanol → 3-Methoxy-4,5,6,7-tetrahydro-1,2-benzisothiazol-4-one

HRID 566460Notes

Reaction equation

HRID 566460 reaction equation
Cl[C:2]1[C:6]2[C:7](=[O:11])[CH2:8][CH2:9][CH2:10][C:5]=2[S:4][N:3]=1.[Na].[CH3:13][OH:14]>>[CH3:13][O:14][C:2]1[C:6]2[C:7](=[O:11])[CH2:8][CH2:9][CH2:10][C:5]=2[S:4][N:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 106551973-Chloro-4,5,6,7-tetrahydro-1,2-benzisothiazol-4-one

Product 1

HCID 108451773-Methoxy-4,5,6,7-tetrahydro-1,2-benzisothiazol-4-one

Procedure

A mixture of 3-chloro-4,5,6,7-tetrahydro-1,2-benzisothiazol-4-one 24a (600 mg) and a solution of sodium (506 mg) in methanol (22 mL) was stirred at 90° C. for 1 h. The reaction mixture was evaporated and water (20 mL) was added to the residue. Extractions with methylene chloride (3×30 mL), drying and evaporation gave an oil. Column chromatography on silica gel (eluent: toluene-ethyl acetate 4:1) gave the title compound (251 mg). Mp 45-46° C.

Workup

  1. customThe reaction mixture was evaporated
  2. additionwater (20 mL) was added to the residue
  3. extractionExtractions with methylene chloride (3×30 mL)
  4. customdrying
  5. customevaporation
  6. customgave an oil

Sources & evidence

ORD record
ord-01e4d5c3848148f2bf9b93c628c8af07
Source dataset
uspto-grants-2001_01
Patent number
US06174909B1

Reaction notes

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