1,3-Butadiene → HCID 21539681, compound

HRID 1076265Notes

Reaction equation

HRID 1076265 reaction equation
Cl.[C:2](=[N:10][OH:11])([Cl:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[CH2:12]=[CH:13][CH:14]=[CH2:15].C(N(CC)CC)C>C(O)C>[ClH:9].[CH:13]([CH:14]1[O:11][N:10]=[C:2]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=2)[CH2:15]1)=[CH2:12]

Participants

5

Reactant 3

HCID 78451,3-ButadieneHCID 8471TriethylamineHCID 85615038HCID 85615038, compound

Product 1

HCID 21539681HCID 21539681, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred suspension of 27.0 g. of nicotinoyl chloride oxime hydrochloride and 30.2 g. of 1,3-butadiene in 500 ml. of absolute ethanol was added dropwise, over a one hour period, a solution of 29.3 g. of triethylamine in 200 ml. of ethanol. The reaction was stirred at room temperature for one hour, the solvent was removed by evaporation and the residue mixed with water and filtered. The solid was dissolved in diethyl ether and washed several times with water. The ether layer was separated, dried over sodium sulfate and filtered to remove solids (drying agent). Removal of the solvent left a red orange liquid which was dissolved in diethyl ether and HCl gas was bubbled in to form a white solid which was collected by filtration and recrystallized from ethanol. Recrystallization was repeated a second time. The hydrochloride salt melts at 201°-204°C.

Workup

  1. additionTo a stirred suspension of 27.0 g
  2. customthe solvent was removed by evaporation
  3. additionthe residue mixed with water
  4. filtrationfiltered
  5. dissolutionThe solid was dissolved in diethyl ether
  6. washwashed several times with water
  7. customThe ether layer was separated
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customto remove
  11. customsolids (drying agent)
  12. customRemoval of the solvent
  13. waitleft a red orange liquid which
  14. dissolutionwas dissolved in diethyl ether
  15. customHCl gas was bubbled in
  16. customto form a white solid which
  17. filtrationwas collected by filtration
  18. customrecrystallized from ethanol
  19. customRecrystallization

Sources & evidence

ORD record
ord-e01dbc3e6afb4852baa2e8a5ff1d9d57
Source dataset
uspto-grants-1976_05
Patent number
US03956343

Reaction notes

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