Iodoethane → HCID 178477479, compound

HRID 1861974Notes

Reaction equation

HRID 1861974 reaction equation
[C:1]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH2:20])=[S:19])=[CH:13][CH:12]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21](I)[CH3:22].C(=O)(O)[O-].[Na+]>C(#N)C>[C:1]([NH:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([NH:17][C:18](=[NH:20])[S:19][CH2:21][CH3:22])=[CH:15][CH:16]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 516892Sodium BicarbonateHCID 18621969HCID 18621969, compound

Product 1

HCID 178477479HCID 178477479, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of N-benzoyl-4-thioureidobenzylamine (139.1 mg) and acetonitrile (10 ml), ethyl iodide (0.5 ml) was added and heated under reflux for 3 h. A saturated aqueous sodium bicarbonate solution was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed successively with water and a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, chloroform:methanol=20:1) to give 134.8 mg of the titled compound (yield, 88%).

Workup

  1. additionwas added
  2. temperatureheated
  3. temperatureunder reflux for 3 h
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed successively with water
  6. dry with materiala saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (eluent, chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-acd0f6ba32ec42c2abcc5fb0634850fe
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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