Sodium Cyanide → 2-[p-(2-Thenoyl)phenyl]acetonitrile

HRID 461719

Reaction equation

HRID 461719 reaction equation
[C-:1]#[N:2].[Na+].[S:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17]Cl)=[CH:13][CH:12]=1)=[O:10]>CS(C)=O>[C:5]1([C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:1]#[N:2])=[CH:13][CH:12]=2)=[O:10])[S:4][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 21391736alpha-Chloro-p-tolyl 2-thienyl ketone

Product 1

HCID 122329742-[p-(2-Thenoyl)phenyl]acetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5.9 parts of sodium cyanide in 40 parts of dimethyl sulfoxide is heated to 60° C and there are added at once 9.5 parts of α-chloro-p-tolyl 2-thienyl ketone (exothermic reaction: temperature rises to 100° C). The whole is stirred for 2 hours at 60° C. After cooling, the reaction mixture is poured onto water and the product is extracted three times with 450 parts of chloroform. The combined extracts are washed twice with 200 parts of water, dried and evaporated. The dark-coloured residual tar is extracted five times with ether; the combined ether extracts are stirred with activated charcoal, filtered and evaporated. The residue is triturated in petroleumether (solid carbon dioxide) and the whole is evaporated, yielding 2-[p-(2-thenoyl)phenyl]acetonitrile as a residue.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture is poured onto water
  3. extractionthe product is extracted three times with 450 parts of chloroform
  4. washThe combined extracts are washed twice with 200 parts of water
  5. customdried
  6. customevaporated
  7. extractionThe dark-coloured residual tar is extracted five times with ether
  8. stirringthe combined ether extracts are stirred with activated charcoal
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue is triturated in petroleumether (solid carbon dioxide)
  12. customthe whole is evaporated

Sources & evidence

ORD record
ord-1193e597455b4cd9918d39b884ea681c
Source dataset
uspto-grants-1977_12
Patent number
US04064132

Linked notes

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