Benzoyl chloride → 4-[3-(N-benzyl-N-benzoylamino)propylthio]pyridine

HRID 863973Notes

Reaction equation

HRID 863973 reaction equation
Cl.Cl.[CH2:3]([NH:10][CH2:11][CH2:12][CH2:13][S:14][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl>[CH2:3]([N:10]([CH2:11][CH2:12][CH2:13][S:14][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 190792264-[3-(N-benzylamino)propylthio]pyridine dihydrochloride

Product 1

HCID 190790974-[3-(N-benzyl-N-benzoylamino)propylthio]pyridineYield 50.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 400 mg (1.21 mmol) of 4-[3-(N-benzylamino)propylthio]pyridine dihydrochloride and 0.55 ml (4.00 mmol) of triiethylamine in 5 ml of methylene chloride, 0.17 ml (1.45 mmol) of benzoyl chloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and water and dried, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 0.22 g of the desired compound (yield: 50.4%, yellow oil).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. washThe reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and water
  4. customdried
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-1f9625e85850467382d62797447f0485
Source dataset
uspto-grants-1996_10
Patent number
US05561147

Reaction notes

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