Tributyltin Chloride → HCID 23449176, compound

HRID 989813Notes

Reaction equation

HRID 989813 reaction equation
C([Li])CCC.CCCCCC.[C:12]([C:18]1[N:19]=[CH:20][N:21]2[CH:25]=[CH:24][S:23][C:22]=12)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14].[CH2:26]([Sn:30](Cl)([CH2:35][CH2:36][CH2:37][CH3:38])[CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH3:29].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[C:12]([C:18]1[N:19]=[CH:20][N:21]2[CH:25]=[C:24]([Sn:30]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:35][CH2:36][CH2:37][CH3:38])[CH2:26][CH2:27][CH2:28][CH3:29])[S:23][C:22]=12)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 23449341HCID 23449341, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 23449176HCID 23449176, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 1.6 N n-butyllithium/n-hexane solution (2.9 ml) was added to a solution of 0.92 g of 7-pivaloylimidazo[5,1-b]thiazole in 20 ml of dry THF in an argon atmosphere at −50° C. The mixture was stirred at the same temperature for 20 min. Tri-n-butylstannyl chloride (1.3 ml) was added thereto, followed by stirring for 20 min. A saturated aqueous ammonium chloride solution was added to the reaction mixture. Ethyl acetate was 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=1:3) to give 0.82 g of the title compound.

Workup

  1. stirringby stirring for 20 min
  2. washThe mixture was washed with water and saturated brine in that order
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-3498ed13018d41c3b879b8bdc35e35ad
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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