Dimethyl Sulfoxide → HCID 13672735, compound

HRID 569004Notes

Reaction equation

HRID 569004 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([CH:9](Cl)Cl)[CH:6]=[CH:5][CH:4]=1)#[N:2].[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-:19].[K+].CS(C)=O>O>[O:18]([CH:9]([O:19][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7]1[N:8]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][CH:6]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 996PhenolHCID 14797Potassium HydroxideHCID 136727346-(Dichloromethyl)pyridine-2-carbonitrile

Product 1

HCID 13672735HCID 13672735, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4.18 g of 6-cyano-2-(dichloromethyl)pyridine, 5.25 g of phenol, 3.33 g of potassium hydroxide and 50 ml of dimethylsulfoxide was heated to 60° C. After a reaction period of about 4 hours, the reaction was complete. The mixture was cooled and poured into 100 ml of water and then extracted with methylene chloride. The solvent extract was run through a bed of silica gel and the solvent removed. The mixture was heated to 160° C. at 0.05 milliliters of mercury. The resulting material was dissolved in a mixture of about 50 ml of methylene chloride filtered and the solvent removed by evaporation under reduced pressure. The above named product was recovered in a yield of 0.95 g and melted at 82°-85° C. The structure of the product was confirmed by its NMR and IR spectrum. Upon analysis, the product was found to have carbon, hydrogen and nitrogen contents of 74.44, 4.72 and 9.05 percent, respectively as compared with the theoretical contents of 75.50, 4.64 and 9.27 percent, respectively as calculated for the above named compound (Compound 28).

Workup

  1. customAfter a reaction period of about 4 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with methylene chloride
  4. extractionThe solvent extract
  5. customthe solvent removed
  6. temperatureThe mixture was heated to 160° C. at 0.05 milliliters of mercury
  7. dissolutionThe resulting material was dissolved in a mixture of about 50 ml of methylene chloride
  8. filtrationfiltered
  9. customthe solvent removed by evaporation under reduced pressure
  10. customwas recovered in a yield of 0.95 g and melted at 82°-85° C

Sources & evidence

ORD record
ord-aaab3bf68e8c443092fa981ff296257b
Source dataset
uspto-grants-1988_03
Patent number
US04731107

Reaction notes

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