Tributyltin Chloride → HCID 23449222, compound

HRID 989808Notes

Reaction equation

HRID 989808 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.[CH2:16]([Sn:20](Cl)([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19].[C:30]([C:34]1[N:35]=[CH:36][N:37]2[CH:41]=[CH:40][S:39][C:38]=12)(=[O:33])[CH2:31][CH3:32].[Cl-].[NH4+]>C1COCC1>[C:30]([C:34]1[N:35]=[CH:36][N:37]2[C:41]([Sn:20]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:40][S:39][C:38]=12)(=[O:33])[CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 23449259HCID 23449259, compoundHCID 23714775LiHMDS tetrahydrofuran2×

Product 1

HCID 23449222HCID 23449222, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A 1.0 N lithiumbis(trimethylsilyl)amide/THF solution (6.17 ml) was added to 60 ml of THF. A solution of 2.12 ml of tri-n-butylstannyl chloride in 24 ml of THF and a solution of 1.11 g of 7-propionylimidazo[5,1-b]thiazole in 24 ml of THF were dropwise added in that order in an argon atmosphere at −73° C. to the mixture. The mixture was stirred at the same temperature for one hr. A 1.0 N lithiumbis(trimethylsilyl)amide/THF solution (6.17 ml) was added dropwise thereto. The mixture was stirred at the same temperature for 2 hr. An ammonium chloride solution (250 ml) was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and 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). Of two main components, the fraction, which had been eluted earlier, was collected to give 234 mg of 7-propionyl-3-(tri-n-butylstannyl)imidazo[5,1-b]thiazole.

Workup

  1. stirringThe mixture was stirred at the same temperature for 2 hr
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1)
  8. washOf two main components, the fraction, which had been eluted earlier
  9. customwas collected

Sources & evidence

ORD record
ord-c561253ea1ba475e83d6366b86db7be7
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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