Methanol → HCID 19806762, compound

HRID 1681469Notes

Reaction equation

HRID 1681469 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:14])[N:5]=1)[CH3:2].C[Si]([NH:19][Si](C)(C)C)(C)C.CO>C(#N)C>[CH2:1]([O:3][C:4]1[C:8]([NH2:19])=[C:7]([S:10]([CH3:13])(=[O:12])=[O:11])[S:6](=[O:14])[N:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 13838HexamethyldisilazaneHCID 19806793HCID 19806793, compound

Product 1

HCID 19806762HCID 19806762, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of crude 3-ethoxy-4-chloro-5- methylsulfonylisothiazole-1-oxide (0.90 g, 1.6 mmol) in acetonitrile (10 ml) under a nitrogen atmosphere was added hexamethyldisilizane (0.70 ml, 3.3 mmol). The reaction mixture was heated at 70° for 11/2 hours, cooled to room temperature and methanol (1.0 ml) was added. The reaction was filtered and evaporated. The residue was triturated with methanol/ethyl acetate to afford crude title compound (0.3 g). Recrystallization from methanol/ethyl acetate after treatment with charcoal gave 0.23 g of pure product, mp 191°-193°.

Workup

  1. temperatureThe reaction mixture was heated at 70° for 11/2 hours
  2. filtrationThe reaction was filtered
  3. customevaporated
  4. customThe residue was triturated with methanol/ethyl acetate
  5. customto afford crude title compound (0.3 g)
  6. customRecrystallization from methanol/ethyl acetate after treatment with charcoal

Sources & evidence

ORD record
ord-7669a562d6ae4e898afdc0e8beb6bbaa
Source dataset
uspto-grants-1992_12
Patent number
US05171860

Reaction notes

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