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

HRID 484624Notes

Reaction equation

HRID 484624 reaction equation
C([Li])CCC.[S:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[CH3:11][Sn:12](Cl)([CH3:14])[CH3:13].C(=O)(O)[O-].[Na+]>CCCCCC.CCOCC>[CH3:11][Sn:12]([CH3:14])([CH3:13])[C:7]1[S:6][CH:10]=[CH:9][N:8]=1

Participants

7

Reactant 4

HCID 9256ThiazoleHCID 14016Trimethyltin chlorideHCID 516892Sodium BicarbonateHCID 178418339Butyllithium

Product 1

HCID 129566412-(Trimethylstannyl)-1,3-thiazoleYield 71.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To 99.99 ml of n-butyl lithium in hexane, dissolved in 200 ml of ether is added dropwise with stirring over 1 hour, at -78° C., a solution of 16 g of thiazole in 100 ml of ether over 1 hour. A solution of 49.81 g of trimethyltin chloride in 100 ml of ether is added dropwise over 20 minutes followed by additional stirring for 1 hour. The reaction mixture is poured into saturated sodium bicarbonate and the organic layer separated, dried and evaporated to a residue. The residue is vacuum distilled to give 33.4 g of the desired product as a colorless liquid, B.P. 60°-65° C./0.7 mm.

Workup

  1. additionis added dropwise
  2. stirringby additional stirring for 1 hour
  3. customthe organic layer separated
  4. customdried
  5. customevaporated to a residue
  6. distillationdistilled

Sources & evidence

ORD record
ord-ae961c498c1b4a708a04bbfb81ec7d78
Source dataset
uspto-grants-1993_07
Patent number
US05231182

Reaction notes

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