Methanol → HCID 19806722, compound

HRID 1681470Notes

Reaction equation

HRID 1681470 reaction equation
[CH2:1]([O:3][C:4]1[C:8](Cl)=[C:7]([S:10]([CH3:13])(=[O:12])=[O:11])[S:6](=[O:15])(=[O:14])[N:5]=1)[CH3:2].C[Si]([NH:20][Si](C)(C)C)(C)C.CO>C(#N)C>[CH2:1]([O:3][C:4]1[C:8]([NH2:20])=[C:7]([S:10]([CH3:13])(=[O:12])=[O:11])[S:6](=[O:15])(=[O:14])[N:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 13838HexamethyldisilazaneHCID 19806737HCID 19806737, compound

Product 1

HCID 19806722HCID 19806722, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-ethoxy-4-chloro-5-methylsulfonylisothiazole-1,1-dioxide (1.1 g, 4.0 mmol) in acetonitrile (15 ml) under a nitrogen atmosphere was added hexamethyldisilizane (0.85 ml, 4.0 mmol). After an immediate exothermic reaction, the solution was heated at gentle reflux for 1 hour. Upon cooling to room temperature, methanol (1.0 ml) was added and any solid removed by filtration. The organic solution was evaporated and the solid residue triturated with ethyl acetate/methanol to give crystalline title compound (0.81 g), mp 214°-217°.

Workup

  1. customAfter an immediate exothermic reaction
  2. temperaturethe solution was heated
  3. temperatureat gentle reflux for 1 hour
  4. customany solid removed by filtration
  5. customThe organic solution was evaporated
  6. customthe solid residue triturated with ethyl acetate/methanol

Sources & evidence

ORD record
ord-82590e6ec89241688e9607a887a8a36c
Source dataset
uspto-grants-1992_12
Patent number
US05171860

Reaction notes

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