Sodium Cyanide → Benzo[b]thiophene-3-acetonitrile

HRID 501208

Reaction equation

HRID 501208 reaction equation
[C-:1]#[N:2].[Na+].Cl[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:8][CH:7]=1>CS(C)=O>[S:8]1[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:6]([CH2:5][C:1]#[N:2])=[CH:7]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 766803-(Chloromethyl)benzo(b)thiophene

Product 1

HCID 76681Benzo[b]thiophene-3-acetonitrileYield 65.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred solution of NaCN (1.4 g, 28.5 mmol) in DMSO (8 mL) was added 3-(chloromethyl)-1-benzothiophene (4 gm, 21.9 mmol) in DMSO (6 mL) over 15 min. The reaction mixture was stirred at room temperature for 18 h and then quenched with water and extracted with ether (2×50 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography using ethyl acetate-hexane (1:1) to furnish 1-benzothien-3-ylacetonitrile (2.5 g, 65%). 1H NMR (200 MHz, CDCl3): δ 3.69 (s, 2H), 7.25-7.91 (m, 5H).

Workup

  1. customquenched with water
  2. extractionextracted with ether (2×50 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9e9a173a102d4360b87ed539b30a777f
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Linked notes

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