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

HRID 461728Notes

Reaction equation

HRID 461728 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]Br)=[CH:13][CH:12]=1)=[O:10]>>[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

3

Reactant 2

HCID 8929Sodium CyanideHCID 12232971Methanone, [4-(bromomethyl)phenyl]-2-thienyl-

Product 1

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

Conditions

Temperature
60 °C

Procedure

A mixture of 5.9 parts of sodium cyanide in 40 parts of dimethyl sufoxide is heated to 60° C and there are added at once 11.3 parts of α-bromo-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 several 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 several 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-e6e1afaa1e5743caafbf3490ef9e5adb
Source dataset
uspto-grants-1977_12
Patent number
US04064132

Reaction notes

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