Ethyl Acetate → HCID 22632004, compound

HRID 1840432Notes

Reaction equation

HRID 1840432 reaction equation
[CH3:1][S:2][C:3]1[N:10]2[C:6]([S:7][CH:8]=[CH:9]2)=[C:5]([S:11][CH3:12])[N:4]=1.C([Li])CCC.CCCCCC.[CH2:24]([Sn:28](Cl)([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH3:27].C(OCC)(=O)C>C1COCC1>[CH3:1][S:2][C:3]1[N:10]2[C:6]([S:7][C:8]([Sn:28]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:24][CH2:25][CH2:26][CH3:27])=[CH:9]2)=[C:5]([S:11][CH3:12])[N:4]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 15096Tributyltin ChlorideHCID 22631779HCID 22631779, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 22632004HCID 22632004, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

5,7-Bis(methylthio)imidazo[5,1-b]thiazole (1.66 g) was dissolved in 50 ml of THF under an argon atmosphere. The solution was cooled to −60° C. A 1.6 N n-butyllithium/n-hexane solution (5.76 ml) and 2.29 ml of tri-n-butylstannyl chloride were added dropwise in that order to the solution, and the temperature of the mixture was raised to −40° C. over a period of one hr. Ethyl acetate (100 ml) was added to the reaction solution, and the mixture was washed with 100 ml of brine. The organic layer was dried over anhydrous magnesium sulfate, and was filtered. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1) to prepare 2.31 g of the title compound.

Workup

  1. temperaturethe temperature of the mixture was raised to −40° C. over a period of one hr
  2. washthe mixture was washed with 100 ml of brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationwas filtered
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1)
  7. customto prepare 2.31 g of the title compound

Sources & evidence

ORD record
ord-efa242a05b214d578e155b460924ecf8
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

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