Tributyltin Chloride → HCID 23449217, compound

HRID 1839286Notes

Reaction equation

HRID 1839286 reaction equation
C([Li])CCC.CCCCCC.[CH3:12][S:13]([C:16]1[N:17]=[CH:18][N:19]2[CH:23]=[CH:22][S:21][C:20]=12)(=[O:15])=[O:14].[CH2:24]([Sn:28](Cl)([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH3:27].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[CH3:12][S:13]([C:16]1[N:17]=[CH:18][N:19]2[CH:23]=[C:22]([Sn:28]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:24][CH2:25][CH2:26][CH3:27])[S:21][C:20]=12)(=[O:14])=[O:15]

Participants

7

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 23448990HCID 23448990, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 23449217HCID 23449217, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 1.6 N n-butyllithium/n-hexane solution (2.8 ml) was added to a solution of 404 mg of 7-methanesulfonylimidazo[5,1-b]thiazole in 20 ml of dry THF in an argon atmosphere at −40° C. The mixture was stirred at the same temperature for 30 min. Tri-n-butylstannyl chloride (0.6 ml) was added thereto. A saturated aqueous ammonium chloride solution was added to the reaction solution. Ethyl acetate was then added thereto. The mixture was washed with water and saturated brine in that order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1) to give 251 mg of the title compound.

Workup

  1. washThe mixture was washed with water and saturated brine in that order
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation
  4. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-16e410124f52472d952da97b7f280d9f
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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