Sodium Cyanide → HCID 21391785, compound

HRID 258936Notes

Reaction equation

HRID 258936 reaction equation
[C-:1]#[N:2].[Na+].[S:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]([C:11]1[C:12]([Cl:19])=[C:13]([CH2:17]Br)[CH:14]=[CH:15][CH:16]=1)=[O:10]>CS(C)=O>[Cl:19][C:12]1[C:11]([C:9](=[O:10])[C:5]2[S:4][CH:8]=[CH:7][CH:6]=2)=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:17][C:1]#[N:2]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 21391797HCID 21391797, compound

Product 1

HCID 21391785HCID 21391785, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred and hot solution of 7.35 parts of sodium cyanide in 50 parts of dimethyl sulfoxide is added dropwise a solution of 15.2 parts of α-bromo-2-chloro-m-tolyl 2-thienyl ketone in 25 parts of dimethyl sulfoxide at 60° C. Upon completion, stirring is continued for 2 hours at 60° C. The reaction mixture is poured onto water and the product is extracted three times with 240 parts of ether. The combined ether phases are washed three times with 100 parts of water, dried, filtered and evaporated. The residue is boiled four times in 80 parts of diisopropylether and the latter is each time decanted, yielding 2-[2-chloro-3-(2-thenoyl)phenyl] acetonitrile as a residue which solidifies on standing.

Workup

  1. stirringUpon completion, stirring
  2. additionThe reaction mixture is poured onto water
  3. extractionthe product is extracted three times with 240 parts of ether
  4. washThe combined ether phases are washed three times with 100 parts of water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customdecanted

Sources & evidence

ORD record
ord-914ed4ff1d8c4368a2eda648e4d5c13a
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Reaction notes

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