Chlorotrimethylsilane → HCID 23449325, compound

HRID 989864Notes

Reaction equation

HRID 989864 reaction equation
C([Li])CCC.CCCCCC.[S:12]1[CH:16]=[CH:15][N:14]2[CH:17]=[N:18][CH:19]=[C:13]12.[CH3:20][Si:21](Cl)([CH3:23])[CH3:22].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[CH3:20][Si:21]([CH3:23])([CH3:22])[C:16]1[S:12][C:13]2=[CH:19][N:18]=[CH:17][N:14]2[CH:15]=1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 25517Ammonium ChlorideHCID 21262404Imidazo[5,1-b]thiazoleHCID 178418244HCID 178418244, compound2×

Product 1

HCID 23449325HCID 23449325, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 1.6 N n-butyllithium/n-hexane solution (16.7 ml) was added in an argon atmosphere at −50° C. to a solution of 3.17 g of imidazo[5,1-b]thiazole in 120 ml of dry THF. The mixture was stirred at the same temperature for 30 min. Trimethylsilyl chloride (3.54 ml) was added thereto, and the mixture was stirred for 20 min. A 1.6 N n-butyllithium/n-hexane solution (8.0 ml) was added thereto, and the mixture was stirred for 20 min. A saturated aqueous ammonium chloride solution was added to the reaction mixture. Ethyl acetate was then added thereto, followed by washing with water and saturated brine in that order. 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 4.53 g of 2-(trimethylsilyl)imidazo[5,1-b]thiazole.

Workup

  1. stirringthe mixture was stirred for 20 min
  2. stirringthe mixture was stirred for 20 min
  3. washby washing with water and saturated brine in that order
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-9c65c9a92d51473486a0f0d57c10b1fd
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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