Tributyltin Chloride → HCID 23449030, compound

HRID 989825Notes

Reaction equation

HRID 989825 reaction equation
[CH2:1]([S:3]([C:6]1[N:7]=[CH:8][N:9]2[CH:13]=[CH:12][S:11][C:10]=12)(=[O:5])=[O:4])[CH3:2].C([Li])CCC.CCCCCC.[CH2:25]([Sn:29](Cl)([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH3:28].[Cl-].[NH4+]>C1COCC1>[CH2:1]([S:3]([C:6]1[N:7]=[CH:8][N:9]2[CH:13]=[C:12]([Sn:29]([CH2:30][CH2:31][CH2:32][CH3:33])([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:25][CH2:26][CH2:27][CH3:28])[S:11][C:10]=12)(=[O:4])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 23449279HCID 23449279, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 23449030HCID 23449030, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 669 mg of 7-ethanesulfonylimidazo[5,1-b]thiazole in 30 ml of THF was cooled to −40° C. in an argon atmosphere. A 1.6 N n-butyllithium/n-hexane solution (4.3 ml) was added dropwise thereto at the same temperature. The mixture was stirred for 15 min. Tri-n-butylstannyl chloride (0.88 ml) was added thereto, followed by stirring at the same temperature for 10 min. A saturated aqueous ammonium chloride solution was added thereto. The mixture was extracted twice with ethyl acetate. The extract was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1). The title compound (1.54 g) was obtained from the fraction of Rf=0.2.

Workup

  1. stirringby stirring at the same temperature for 10 min
  2. extractionThe mixture was extracted twice with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-de56152491884e9bba0d1b370a76be3c
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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