Tributyltin Chloride → 7-p-Toluenesulfonyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole

HRID 1839294Notes

Reaction equation

HRID 1839294 reaction equation
[C:1]1([CH3:18])[CH:6]=[CH:5][C:4]([S:7]([C:10]2[N:11]=[CH:12][N:13]3[CH:17]=[CH:16][S:15][C:14]=23)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C([Li])CCC.CCCCCC.[CH2:30]([Sn:34](Cl)([CH2:39][CH2:40][CH2:41][CH3:42])[CH2:35][CH2:36][CH2:37][CH3:38])[CH2:31][CH2:32][CH3:33].[Cl-].[NH4+]>C1COCC1>[C:1]1([CH3:18])[CH:2]=[CH:3][C:4]([S:7]([C:10]2[N:11]=[CH:12][N:13]3[CH:17]=[C:16]([Sn:34]([CH2:35][CH2:36][CH2:37][CH3:38])([CH2:39][CH2:40][CH2:41][CH3:42])[CH2:30][CH2:31][CH2:32][CH3:33])[S:15][C:14]=23)(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 234492047-p-Toluenesulfonylimidazo[5,1-b]thiazoleHCID 178418244HCID 178418244, compound

Product 1

HCID 234490517-p-Toluenesulfonyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazoleYield 43.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of: 669 mg of 7-p-toluenesulfonylimidazo[5,1-b]thiazole in 65 ml of THF was cooled to −60° C. in an argon atmosphere. A 1.6 N n-butyllithium/n-hexane solution (2.5 ml) was added dropwise thereto at the same temperature. The mixture was stirred for 20 min. A solution of 1.25 g of tri-n-butylstannyl chloride in 10 ml of THF was added thereto, and the mixture was stirred at the same temperature for 40 min. A semisaturated aqueous ammonium chloride solution (150 ml), was added thereto, followed by extraction with 250 ml of 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 (590 mg) was obtained from the fraction of Rf=0.4.

Workup

  1. stirringthe mixture was stirred at the same temperature for 40 min
  2. extractionfollowed by extraction with 250 ml of 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-970d29aa44ca4c70b7ffe2db63a53d1a
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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