Water → HCID 18975698, compound

HRID 1409014Notes

Reaction equation

HRID 1409014 reaction equation
[H-].[Na+].[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][C:9]#[N:10].Br[CH2:12][CH2:13]Cl.O>CS(C)=O>[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1([C:9]#[N:10])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 78491-Bromo-2-ChloroethaneHCID 24758Sodium hydrideHCID 728802-Thienylacetonitrile

Product 1

HCID 18975698HCID 18975698, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To a suspension of sodium hydride (19.1 g) in DMSO (200 mL) was added dropwise a solution of thiophen-2-ylacetonitrile (25 g) in DMSO (20 mL) at 0° C. under a nitrogen atmosphere, and the mixture was stirred for 0.5 hr. To the obtained reaction mixture was added dropwise a solution of 1-bromo-2-chloroethane (25 mL) in DMSO (20 mL) at 0° C. under a nitrogen atmosphere, and the mixture was stirred at room temperature for 3 days. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound as a pale-brown oil (29.2 g).

Workup

  1. customTo the obtained reaction mixture
  2. stirringthe mixture was stirred at room temperature for 3 days
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e777ab27843141498014dd4c0ec36d63
Source dataset
uspto-grants-2014_12
Patent number
US08921354B2

Reaction notes

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