TBAF tetrahydrofuran → HCID 23449275, compound

HRID 989863Notes

Reaction equation

HRID 989863 reaction equation
[CH3:1][S:2][C:3]1[N:4]2[CH:14]=[N:13][C:12]([S:15][CH3:16])=[C:5]2[S:6][C:7]=1[Si](C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>C1COCC1.[Cl-].[Na+].O>[CH3:1][S:2][C:3]1[N:4]2[CH:14]=[N:13][C:12]([S:15][CH3:16])=[C:5]2[S:6][CH:7]=1

Participants

5

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 23449070HCID 23449070, compound

Product 1

HCID 23449275HCID 23449275, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 1.88 g of 3,7-bis(methylthio)-2-trimethylsilylimidazo[5,1-b]thiazole in 50 ml of THF was ice cooled. A 1 M tetra-n-butylammonium fluoride/THF solution (8.16 ml) was added in an argon atmosphere to the solution. The mixture was stirred at the same temperature for one hr. Brine was added thereto, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with brine, 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=1:1) to give 1.30 g of 3,7-bis(methylthio)imidazo[5,1-b]thiazole.

Workup

  1. temperaturecooled
  2. extractionthe mixture was extracted twice 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=1:1)

Sources & evidence

ORD record
ord-2b706b6f5df8422596e81f450ad6d0bd
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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