Benzoyl chloride → 4-[4-(Benzoylamino)butylthio]pyridine

HRID 2210174Notes

Reaction equation

HRID 2210174 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[C:20]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 135575374-[(Pyridin-4-yl)sulfanyl]butan-1-amine

Product 1

HCID 190791704-[4-(Benzoylamino)butylthio]pyridineYield 34.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.00 g (5.49 mmol) of 4-(4-aminobutylthio)pyridine and 0.92 ml (6.60 mmol) of triethylamine in 30 ml of methylene chloride, 0.67 ml (5.77 mmol) of benzoyl chloride was added with stirring under ice-cooling and the mixture was stirred at room temperature for 13 hours. The mixture was washed with saturated aqueous sodium bicarbonate and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate) to give 0.54 g of the desired compound (34.4% yield, colorless crystals), mp. 75°-77° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 13 hours
  3. washThe mixture was washed with saturated aqueous sodium bicarbonate and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-60db8ed9768d4eca8062ff52bab03fc6
Source dataset
uspto-grants-1995_10
Patent number
US05457106

Reaction notes

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