Benzoyl chloride → 4-[3-(N-(2-thienylmethyl)-N-benzoylamino)propylthio]pyridine

HRID 863983Notes

Reaction equation

HRID 863983 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][CH2:8][CH2:9][CH2:10][S:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]([CH2:8][CH2:9][CH2:10][S:11][C:12]1[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=1)[C:25](=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 190791844-(3-(N-(2-thienylmethyl)amino)propylthio]pyridine

Product 1

HCID 190791174-[3-(N-(2-thienylmethyl)-N-benzoylamino)propylthio]pyridineYield 35.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2..5 g (9.45 mmol) of 4-[3-(N-(2-thienylmethyl)amino)propylthio]pyridine and 1.32 ml (9.45 mmol) of triethylamine in 50 ml of methylene chloride, 1.1 ml (9.45 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 the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 1.25 g of the desired compound (yield: 35.9%, 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-00943ad703184e6b89c0f98563d42ece
Source dataset
uspto-grants-1996_10
Patent number
US05561147

Reaction notes

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