Selenium Dioxide → HCID 13015401, compound

HRID 262443Notes

Reaction equation

HRID 262443 reaction equation
CC1[CH:7]=[CH:6][C:5]([C:8]([Cl:12])=[C:9]([Cl:11])[Cl:10])=[CH:4][N:3]=1.[Se](=O)=[O:14].[O:16]1[CH2:21][CH2:20]OCC1>C(OCC)(=O)C>[Cl:12][C:8]([C:5]1[CH:6]=[CH:7][C:20]([C:21]([OH:16])=[O:14])=[N:3][CH:4]=1)=[C:9]([Cl:11])[Cl:10]

Participants

5

Reactant 3

HCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 13015400HCID 13015400, compound

Product 1

HCID 13015401HCID 13015401, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

G. (0.0050 moles) of 2-methyl 5-trichlorovinyl pyridine is added at room temperature with stirring to 833 mg. (0.0075 moles) of selenium dioxide suspended in 5 ml. of dioxane. The reaction mixture is refluxed for 8 hours and stirred at room temperature overnight. The reaction mixture is filtered through a filtration medium (diatomaceous earth) and the filtration evaporated to dryness in vacuo affording a reddish solid. The solid is taken up in a minimum amount of hot ethyl acetate and filtered. Upon cooling, crystals are obtained which are filtered and washed with ethyl acetate and dried affording 500 mg. of a tan solid with a m.p. of 158°-159° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 8 hours
  2. stirringstirred at room temperature overnight
  3. filtrationThe reaction mixture is filtered through a filtration medium (diatomaceous earth)
  4. filtrationthe filtration
  5. customevaporated to dryness in vacuo
  6. customaffording a reddish solid
  7. filtrationfiltered
  8. temperatureUpon cooling
  9. customcrystals are obtained which
  10. filtrationare filtered
  11. washwashed with ethyl acetate
  12. customdried
  13. customaffording 500 mg

Sources & evidence

ORD record
ord-cb804f00c509472f835410893328a6d8
Source dataset
uspto-grants-1979_05
Patent number
US04154835

Reaction notes

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