Dimethyl Sulfoxide → HCID 21391784, compound

HRID 258898Notes

Reaction equation

HRID 258898 reaction equation
[C-:1]#[N:2].[Na+].CS(C)=O.[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]([C:15]1[CH:16]=[C:17]([CH:21](Cl)[CH3:22])[CH:18]=[CH:19][CH:20]=1)=[O:14]>O>[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]([C:15]1[CH:16]=[C:17]([CH:21]([C:1]#[N:2])[CH3:22])[CH:18]=[CH:19][CH:20]=1)=[O:14]

Participants

5

Reactant 3

HCID 679Dimethyl Sulfoxide3×HCID 8929Sodium CyanideHCID 21391745HCID 21391745, compound

Product 1

HCID 21391784HCID 21391784, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and hot mixture of 2.7 parts of sodium cyanide in 20 parts of dimethylsulfoxide is added dropwise a solution of 5.8 parts of α-chloro-α-methyl-m-tolyl 2-thienyl ketone in 10 parts of dimethylsulfoxide at 60° C. Another 5 parts of dimethylsulfoxide is added and the whole is stirred for 2.5 hours at 50°-55° C. The reaction mixture is poured onto 35 parts of water and the product is extracted with ether and ethyl acetate. The combined organic layers are washed with water, dried, filtered and evaporated in vacuo. The residue is dissolved in benzene. This solution is washed with water, dried and evaporated in vacuo, yielding m-(2-thenoyl)hydratroponitrile, also named α-cyano-α-methyl-m-tolyl 2-thienyl ketone, as a residue.

Workup

  1. stirringthe whole is stirred for 2.5 hours at 50°-55° C
  2. extractionthe product is extracted with ether and ethyl acetate
  3. washThe combined organic layers are washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. dissolutionThe residue is dissolved in benzene
  8. washThis solution is washed with water
  9. customdried
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-9f715b21247f4c248b69beb14ff0d07b
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Reaction notes

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