Tributyltin Chloride → HCID 18359836, compound

HRID 382604Notes

Reaction equation

HRID 382604 reaction equation
C([Li])CCC.CCCCCC.[CH3:12][C:13]1[N:20]2[C:16]([S:17][CH:18]=[CH:19]2)=[C:15]([CH3:21])[N:14]=1.[CH2:22]([Sn:26](Cl)([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25]>C1COCC1>[CH3:12][C:13]1[N:20]2[C:16]([S:17][C:18]([Sn:26]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:22][CH2:23][CH2:24][CH3:25])=[CH:19]2)=[C:15]([CH3:21])[N:14]=1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 18359996HCID 18359996, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 18359836HCID 18359836, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

To 50 ml of anhydrous THF cooled to −65° C. under the atmosphere of argon was added 10.9 ml of a 1.63 N n-butyl lithium/n-hexane solution, and a solution of 2.564 g of 5,7-dimethylimidazo[5,1-b]thiazole in 17 ml of anhydrous THF was further added dropwise at −64-−60° C. over a period of 15 minutes. The reaction mixture was then stirred at the same temperature for 80 minutes. After 5.0 ml of tri-n-butylstannyl chloride was added dropwise to the mixture at a temperature of −63-−58° C. over a period of 10 minutes, it was warmed to −30° C., and further stirred for 110 minutes. The reaction mixture was diluted with 100 ml of semi-saturated aqueous saline, extracted with 150 ml of ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure. The oil thus obtained was purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1-−1:2) to give the title compound as a light orange oil in a yield of 6.164 g.

Workup

  1. stirringfurther stirred for 110 minutes
  2. additionThe reaction mixture was diluted with 100 ml of semi-saturated aqueous saline
  3. extractionextracted with 150 ml of ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe oil thus obtained
  8. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1-−1:2)

Sources & evidence

ORD record
ord-dccae6e975464275a494d761bfa5be2b
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

Loading…