Sodium Cyanide → 2-(5-Chloro-2-phenyl-1-benzothiophen-3-yl)acetonitrile

HRID 985757Notes

Reaction equation

HRID 985757 reaction equation
[C-:1]#[N:2].[Na+].Br[CH2:5][C:6]1[C:10]2[CH:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=2[S:8][C:7]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CS(C)=O>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]2[S:8][C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:6]([CH2:5][C:1]#[N:2])[C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 219167743-Bromomethyl-5-chloro-2-phenylbenzo[b]thiophene

Product 1

HCID 219172462-(5-Chloro-2-phenyl-1-benzothiophen-3-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

1.2 eq. of NaCN are suspended in 20 ml of dimethyl sulphoxide. The mixture is heated at 60° C. for 30 minutes and then 1 eq. of the compound obtained in Step C is added gradually. The reaction mixture is stirred for 1 hour at 60° C. and is then hydrolysed. Extraction with ethyl acetate is carried out and the organic phase is washed with water, dried over MgSO4 and evaporated under reduced pressure. The residue obtained is purified by chromatography on silica gel.

Workup

  1. extractionExtraction with ethyl acetate
  2. washthe organic phase is washed with water
  3. dry with materialdried over MgSO4
  4. customevaporated under reduced pressure
  5. customThe residue obtained
  6. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-4a36b8352b13493bbb9a806de8627293
Source dataset
uspto-grants-2005_03
Patent number
US06872851B1

Reaction notes

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