Hexamethyldisilazane → HCID 19806710, compound

HRID 1681464Notes

Reaction equation

HRID 1681464 reaction equation
C(O[C:4]1[C:8]([O:9][CH2:10][CH3:11])=[C:7]([C:12](=[O:16])[N:13]([CH3:15])[CH3:14])[S:6](=[O:18])(=[O:17])[N:5]=1)C.C[Si]([NH:23][Si](C)(C)C)(C)C>C(#N)C>[NH2:23][C:4]1[C:8]([O:9][CH2:10][CH3:11])=[C:7]([C:12](=[O:16])[N:13]([CH3:15])[CH3:14])[S:6](=[O:18])(=[O:17])[N:5]=1

Participants

4

Reactant 2

HCID 13838HexamethyldisilazaneHCID 19806753HCID 19806753, compound

Product 1

HCID 19806710HCID 19806710, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 60% pure 3,4-diethoxy-5-dimethylcarbamylisothiazole-1,1-dioxide (1.3 g) from Part C in acetonitrile (7 ml), under nitrogen, was added hexamethyldisilizane (0.90%, 4.3 mmol). This solution was heated at 50° for four hours. The reaction was then quenched with methanol (0.5 ml) and the solvent evaporated. This residue was chromatographed on silica gel eluting with 40% methanol/chloroform and the collected product residue triturated with ether to give 0.61 g, of title compound (mp 221°-223°).

Workup

  1. temperatureThis solution was heated at 50° for four hours
  2. customThe reaction was then quenched with methanol (0.5 ml)
  3. customthe solvent evaporated
  4. customThis residue was chromatographed on silica gel eluting with 40% methanol/chloroform
  5. customthe collected product residue triturated with ether
  6. customto give 0.61 g

Sources & evidence

ORD record
ord-56e5c7af31014e7e8d8dccae38dc3849
Source dataset
uspto-grants-1992_12
Patent number
US05171860

Reaction notes

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