Thiazole → 2-(Tributylstannyl)-1,3-thiazole

HRID 2220118Notes

Reaction equation

HRID 2220118 reaction equation
C([Li])CCC.[S:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[CH2:11]([Sn:15](Cl)([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH3:14]>CCOCC>[CH2:20]([Sn:15]([CH2:11][CH2:12][CH2:13][CH3:14])([CH2:16][CH2:17][CH2:18][CH3:19])[C:7]1[S:6][CH:10]=[CH:9][N:8]=1)[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 9256ThiazoleHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Product 1

HCID 27632592-(Tributylstannyl)-1,3-thiazole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (1.6M, 5.3 mL, 8.37 mmol) was added to a solution of thiazole (450 mg, 5.23 mmol) in anhydrous ether (30 mL) stirred −78° C. under nitrogen. After 30 min tri-n-butylstannyl chloride (2.73 g, 8.37 mmol) was added, then the solution was allowed to warm to room temperature, and stirred for another 1 h. The mixture was quenched and washed with 1N sodium hydroxide, dried through MgSO4, and then the solvent was evaporated to give the sub-title compound a brown oily residue (2.0 g), which was used in the next step without further purification.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for another 1 h
  3. customThe mixture was quenched
  4. washwashed with 1N sodium hydroxide
  5. dry with materialdried through MgSO4
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9486492908a2434dab9ce89b34fbfeab
Source dataset
uspto-grants-2008_08
Patent number
US07417050B2

Reaction notes

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