Hydrochloric Acid → 5-(Tributylstannyl)-1,3-thiazole

HRID 2061111Notes

Reaction equation

HRID 2061111 reaction equation
[Li]CCCC.Br[C:7]1[S:11][CH:10]=[N:9][CH:8]=1.[Sn:12](Cl)([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH2:15][CH3:16].Cl>C1COCC1.CCCCCC>[CH2:21]([Sn:12]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:17][CH2:18][CH2:19][CH3:20])[C:7]1[S:11][CH:10]=[N:9][CH:8]=1)[CH2:22][CH2:23][CH3:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 15096Tributyltin ChlorideHCID 5460595-BromothiazoleHCID 178418339Butyllithium

Product 1

HCID 27632575-(Tributylstannyl)-1,3-thiazoleYield 34.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A hexane solution of n-BuLi (4.14 mL, 10 mmol) was added dropwise to an anhydrous tetrahydrofuran solution of 5-bromothiazole (0.46 mL, 5.0 mmol) at −78° C. under nitrogen atmosphere over a period of 30 minutes, and the mixture was stirred for 1 hour. A solution of n-Bu3SnCl (1.41 mL, 5.0 mmol) in THF was then added dropwise over a period of 30 minutes at −78° C., and after stirring for 2 hours, the mixture was raised to room temperature and stirred for another hour. Three drops of a 1N HCl solution were added, and the organic layer was extracted from the aqueous layer twice with 10 mL of ether. The solvent was distilled away to yield the title compound (650 mg, 35 mL).

Workup

  1. stirringafter stirring for 2 hours
  2. stirringstirred for another hour
  3. extractionthe organic layer was extracted from the aqueous layer twice with 10 mL of ether
  4. distillationThe solvent was distilled away

Sources & evidence

ORD record
ord-58a5f907689443f8ab5b91fbf571fd91
Source dataset
uspto-grants-2012_10
Patent number
US08278465B2

Reaction notes

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