Iodoethane → HCID 178475109, compound

HRID 2286188Notes

Reaction equation

HRID 2286188 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([NH:9][OH:10])=[O:8].[H-].[Na+].[CH2:13](I)[CH3:14]>C(O)C>[CH2:13]([O:10][N:9]=[C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[OH:8])[CH3:14]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 147399Picolinohydroxamic acid

Product 1

HCID 178475109HCID 178475109, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7 g (0.05 mol) of pyridine-2-hydroxamic acid and 1.4 g (0.05 mol) of sodium hydride were dissolved in 100 ml of ethanol, and 8 g (0.05 mol) of ethyl iodide was gradually dropwise added thereto with stirring. After the dropwise addition, the reaction solution was stirred for 2 hours under reflux condition. After completion of the reaction, the ethanol was distilled off under reduced pressure. To the residue were added suitable amounts of methylene chloride and water, whereby the desired product was extracted with the methylene chloride. The extract was washed with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. After the drying, the solvent was distilled off under reduced pressure to obtain 8.2 g of the desired product.

Workup

  1. additionAfter the dropwise addition
  2. stirringthe reaction solution was stirred for 2 hours
  3. temperatureunder reflux condition
  4. customAfter completion of the reaction
  5. distillationthe ethanol was distilled off under reduced pressure
  6. additionTo the residue were added suitable amounts of methylene chloride and water, whereby the desired product
  7. extractionwas extracted with the methylene chloride
  8. washThe extract was washed with a saturated sodium chloride aqueous solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationAfter the drying, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f81bbc828061408a8a6798b18b52b41e
Source dataset
uspto-grants-1982_04
Patent number
US04327089

Reaction notes

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