Tributyltin Chloride → HCID 23449140, compound

HRID 989840Notes

Reaction equation

HRID 989840 reaction equation
[CH3:1][C:2]1[N:9]2[C:5]([S:6][CH:7]=[CH:8]2)=[C:4]([S:10][CH3:11])[N:3]=1.C([Li])CCC.CCCCCC.[CH2:23]([Sn:27](Cl)([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH3:26].[Cl-].[NH4+]>C1COCC1>[CH3:1][C:2]1[N:9]2[C:5]([S:6][CH:7]=[C:8]2[Sn:27]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:23][CH2:24][CH2:25][CH3:26])=[C:4]([S:10][CH3:11])[N:3]=1

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 22631854HCID 22631854, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 23449140HCID 23449140, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Methyl-7-methylthioimidazo[5,1-b]thiazole (3.34 g) was dissolved in 150 ml of THF. A 1.59 N n-butyllithium/n-hexane solution (22.8 ml) was added dropwise to the solution in an argon atmosphere at −73° C. The mixture was stirred at the same temperature for 40 min. Tri-n-butylstannyl chloride (6.39 ml) was added thereto, followed by stirring at the same temperature for one hr. An ammonium chloride solution was added to the reaction solution. The mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and then filtered. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1 to 1:1). Of two main components, the fraction, which had been eluted earlier, was collected to give 598 mg of 5-methyl-7-methylthio-3-(tri-n-butylstannyl)imidazo[5,1-b]thiazole.

Workup

  1. stirringby stirring at the same temperature for one hr
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1 to 1:1)
  7. washOf two main components, the fraction, which had been eluted earlier
  8. customwas collected

Sources & evidence

ORD record
ord-228305b830864c899257d41676bef878
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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