Tributyltin Chloride → 2-(Tri-n-butylstannyl)-3-methylimidazo[5,1-b]thiazole

HRID 382593Notes

Reaction equation

HRID 382593 reaction equation
[CH3:1][C:2]1[N:3]2[CH:9]=[N:8][CH:7]=[C:4]2[S:5][CH:6]=1.C([Li])CCC.[CH2:15]([Sn:19](Cl)([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18]>C1COCC1.CCCCCC.[Cl-].[NH4+]>[CH2:24]([Sn:19]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:20][CH2:21][CH2:22][CH3:23])[C:6]1[S:5][C:4]2=[CH:7][N:8]=[CH:9][N:3]2[C:2]=1[CH3:1])[CH2:25][CH2:26][CH3:27]

Participants

7

Reactant 3

HCID 15096Tributyltin ChlorideHCID 22631500HCID 22631500, compoundHCID 178418339Butyllithium

Product 1

HCID 183598392-(Tri-n-butylstannyl)-3-methylimidazo[5,1-b]thiazole

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A solution of 3-methylimidazo[5,1-b]thiazole (513.2 mg) in anhydrous THF (8 ml) was cooled to −78° C. under the atmosphere of argon, and a 1.6 N solution of n-butyl lithium in n-hexane (2.47 ml) was added dropwise. After the reaction was stirred at the same temperature for 1 hour, 1.06 ml of tri-n-butylstannyl chloride was added, and the mixture was further stirred at the same temperature for 1 hour and then for 30 minutes during which the mixture was allowed to be warmed to room temperature. The reaction mixture was diluted with 50 ml of a semi-saturated aqueous ammonium chloride solution, and extracted with 50 ml of diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then removed under reduced pressure. The residue thus obtained was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to give 2-(tri-n-butylstannyl)-3-methylimidazo[5,1-b]thiazole in a yield of 1.44 g.

Workup

  1. stirringthe mixture was further stirred at the same temperature for 1 hour
  2. waitfor 30 minutes during which the mixture was allowed
  3. extractionextracted with 50 ml of diethyl ether
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was then removed under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-7aae55daa3014494911572666d6aca48
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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