Ethyl Acetate → HCID 23449265, compound

HRID 1839330Notes

Reaction equation

HRID 1839330 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.[CH3:24][S:25][C:26]1[N:27]2[CH:37]=[N:36][CH:35]=[C:28]2[S:29][C:30]=1[Si](C)(C)C.C(OCC)(=O)C>C1COCC1.[Cl-].[Na+].O>[CH3:24][S:25][C:26]1[N:27]2[CH:37]=[N:36][CH:35]=[C:28]2[S:29][CH:30]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 11078149TBAF tetrahydrofuranHCID 23449022HCID 23449022, compound

Product 1

HCID 23449265HCID 23449265, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A 1 M Tetra-n-butylammonium fluoride/THF solution (20.0 ml) was added in an argon atmosphere at room temperature to a solution of 3.87 g of 3-methylthio-2-(trimethylsilyl)imidazo[5,1-b]-thiazole in 70 ml of dry THF. The mixture was stirred at the same temperature for 15 min. Semi-saturated brine was added to the reaction mixture. Ethyl acetate was then added thereto, followed by washing with semi-saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (ethyl acetate) to give 2.62 g of 3-methylthioimidazo[5,1-b]thiazole.

Workup

  1. washby washing with semi-saturated brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation
  4. customThe residue was purified by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-05d1c9dc512e497fa553b0d07a19db05
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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