Hexamethyldisilazane → HCID 19806769, compound

HRID 1681472Notes

Reaction equation

HRID 1681472 reaction equation
[CH2:1]([O:3][C:4]1[C:8](Br)=[C:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[S:6](=[O:18])(=[O:17])[N:5]=1)[CH3:2].C[Si](C)(C)[NH:21][Si](C)(C)C>C(#N)C>[CH2:1]([O:3][C:4]1[C:8]([NH2:21])=[C:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[S:6](=[O:18])(=[O:17])[N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 13838HexamethyldisilazaneHCID 19806692HCID 19806692, compound

Product 1

HCID 19806769HCID 19806769, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 3-ethoxy-4-bromo-5-t-butyloxycarbonylisothiazole-1,1-dioxide (340 mg, 1.0 mmol) in 5 ml of dry acetonitrile was added hexamethyldisilazane (242 mg, 1.5 mmol) and the solution was stirred at reflux for 7 hours. The reaction mixture was evaporated in vacuo and the residue was refluxed in 10 ml of ethanol for 3/4 hr. Removal of the ethanol in vacuo gave a crude oil which was chromatographed on silica gel. The product was recovered as a viscous yellow oil (210 mg). Trituration in petroleum ether gave a yellow solid, m.p. 128°-130° C. Mass spectral analysis confirmed the structure.

Workup

  1. temperatureat reflux for 7 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. temperaturethe residue was refluxed in 10 ml of ethanol for 3/4 hr
  4. customRemoval of the ethanol in vacuo
  5. customgave a crude oil which
  6. customwas chromatographed on silica gel
  7. customThe product was recovered as a viscous yellow oil (210 mg)
  8. customTrituration in petroleum ether gave a yellow solid, m.p. 128°-130° C

Sources & evidence

ORD record
ord-7e45e6d7bb7146eb9bab4e4877858c5f
Source dataset
uspto-grants-1992_12
Patent number
US05171860

Reaction notes

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