Water → 1,2-bis[N-[4-(4-pyridylthio)butyl]-N-propionylamino]benzene

HRID 6187

Reaction equation

HRID 6187 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl[CH2:11][CH2:12][CH2:13][CH2:14][N:15]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]([C:32](=[O:35])[CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH2:30]Cl)[C:16](=[O:19])[CH2:17][CH3:18].O>CS(C)=O>[N:5]1[CH:6]=[CH:7][C:2]([S:1][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:26]([C:32](=[O:35])[CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH2:30][S:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[C:16](=[O:19])[CH2:17][CH3:18])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 190792541,2-bis[N-(4-chlorobutyl)-N-propionylamino]benzeneHCID 178418431pyridine-4-thiol

Product 1

HCID 190791281,2-bis[N-[4-(4-pyridylthio)butyl]-N-propionylamino]benzeneYield 81%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 525 mg (4.7 mmol) of 4-mercaptopyridine and 265 mg (4.7 mmol) of potassium hydroxide in 20 ml of dimethyl sulfoxide, 760 mg (1.89 mmol) of 1,2-bis[N-(4-chlorobutyl)-N-propionylamino]benzene was added at room temperature, and the mixture was stirred for 2 hours. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The extract was dried and the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate to ethyl acetate/ethanol =20:1 to 10:1 to 5:1) to give 0.84 g of the desired product (81.0% yield, pale yellow crystals).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe extract was dried
  3. distillationthe solvent was distilled off
  4. customThe residue was purified by column chromatography (eluent: ethyl acetate to ethyl acetate/ethanol =20:1 to 10:1 to 5:1)

Sources & evidence

ORD record
ord-037000249bf248819c335444fe0d73ae
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Linked notes

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