Methane → HCID 15580676, compound

HRID 544634Notes

Reaction equation

HRID 544634 reaction equation
[Na].Cl.[F:3][C:4]1[CH:5]=[C:6]([NH:10][NH2:11])[CH:7]=[CH:8][CH:9]=1.[C:12](#[N:16])[C:13]([CH3:15])=[CH2:14].C>CCCCCC.C(O)C>[NH2:16][C:12]1[CH:13]([CH3:15])[CH2:14][N:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([F:3])[CH:5]=2)[N:11]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 31368MethacrylonitrileHCID 27239143-Fluorophenylhydrazine hydrochlorideHCID 5360545Sodium

Product 1

HCID 15580676HCID 15580676, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Procedure

A 1.38 g. amount of sodium metal is dissolved in 150 ml. of absolute ethanol, then 8.1 g. of m-fluorophenylhydrazine hydrochloride is added followed by 3.9 g. of methacrylonitrile. The reaction mixture is refluxed for 5 hours, then is evaporated to dryness in vacuo. Water is added to give a dark semi-solid precipitate. The aqueous is decanted then more water is added and the solid is collected by filtration. The solid is dissolved in dichloromethane and the solution is passed through a short column of a hydrous magnesium silicate. The effluent is evaporated to give an oil. The oil is dissolved in hexane, treated with activated charcoal and filtered and evaporated to give a solid. The solid is recrystallized from hexane to give 0.65 g. of the desired product as light orange prisms, m.p. 78°-80° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 5 hours
  2. customis evaporated to dryness in vacuo
  3. additionWater is added
  4. customto give a dark semi-solid precipitate
  5. customThe aqueous is decanted
  6. additionmore water is added
  7. filtrationthe solid is collected by filtration
  8. dissolutionThe solid is dissolved in dichloromethane
  9. customThe effluent is evaporated
  10. customto give an oil
  11. filtrationfiltered
  12. customevaporated
  13. customto give a solid
  14. customThe solid is recrystallized from hexane
  15. customto give 0.65 g

Sources & evidence

ORD record
ord-35a5766bf0d84a82a736e0dee4993f43
Source dataset
uspto-grants-1984_05
Patent number
US04451479

Reaction notes

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