Sodium Chloride → HCID 15507634, compound

HRID 440331Notes

Reaction equation

HRID 440331 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C(N(CC)CC)C.[CH:14]#[C:15][CH2:16][CH2:17][CH2:18][CH3:19].[Na+].[Cl-]>[Cu]I.CCOCC.O.C(#N)C>[C:14]([C:2]1[S:3][CH:4]=[CH:5][N:6]=1)#[C:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

9

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 127321-HexyneHCID 764302-Bromothiazole

Product 1

HCID 15507634HCID 15507634, compoundYield 36%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

2-Bromothiazole (6.09 mmol, 1.0 g) was added to 40 mL of acetonitrile. CuI (1.52 mmol, 0.29 g), triethylamine (7.31 mmol, 1.01 mL) and bistriphenylphosphine palladium chloride (0.3 mmol, 0.21 g) were added and the solution degassed. Hexyne (6.09 mmol, 0.7 mL) was added and the mixture heated at refluxed overnight. Water was added followed by NaCl and ether. The layers were separated and the aqueous layer extracted with ether (4x). The organic layers were combined, dried (MgSO4), filtered and concentrated. The residue was subjected to flash chromatography (10% ethyl acetate/hexane) to afford 0.36 g (36%) of 2-(1-hexynyl)thiazole.

Workup

  1. customthe solution degassed
  2. temperaturethe mixture heated
  3. temperatureat refluxed overnight
  4. customThe layers were separated
  5. extractionthe aqueous layer extracted with ether (4x)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0fa8d106ba924b8b9c6a181e86a1a791
Source dataset
uspto-grants-1996_05
Patent number
US05519040

Reaction notes

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