Hexamethyldisilazane → HCID 19806734, compound

HRID 1681482Notes

Reaction equation

HRID 1681482 reaction equation
[CH2:1]([O:3][C:4]1[C:8](Br)=[C:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[S:6](=[O:21])(=[O:20])[N:5]=1)[CH3:2].C[Si](C)(C)[NH:24][Si](C)(C)C>C(#N)C>[CH2:1]([O:3][C:4]1[C:8]([NH2:24])=[C:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[S:6](=[O:21])(=[O:20])[N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 13838Hexamethyldisilazane2×HCID 19806690HCID 19806690, compound

Product 1

HCID 19806734HCID 19806734, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 3-ethoxy-4-bromo-5-benzyloxycarbonylisothiazole-1,1-dioxide (1.50 g, 0.0040 mol) in acetonitrile (6 ml) there was added hexamethyldisilazane (0.91 ml, 0.0043 mol). The mixture was heated at 70° for 3.5 hours. Additional hexamethyldisilazane (0.21 ml, 0.0010 mol) was added and the solution stirred at 70° for 1.5 hours. The mixture was then concentrated to dryness in vacuo and the residue dissolved in ethanol (50 ml) and stirred for 15 minutes. The solution was concentrated to dryness in vacuo and the residue recrystallized from ethanol to give the title product (0.95 g, 77%, mp 149°-151°).

Workup

  1. temperatureThe mixture was heated at 70° for 3.5 hours
  2. concentrationThe mixture was then concentrated to dryness in vacuo
  3. dissolutionthe residue dissolved in ethanol (50 ml)
  4. stirringstirred for 15 minutes
  5. concentrationThe solution was concentrated to dryness in vacuo
  6. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-85766fdd32b248e2a1370c20b7db34e2
Source dataset
uspto-grants-1992_12
Patent number
US05171860

Reaction notes

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