Water → HCID 131716563, compound

HRID 2248410Notes

Reaction equation

HRID 2248410 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[C:15](=[O:18])([O-:17])[O-:16].[K+].[K+].Cl[CH2:22][CH2:23][CH2:24][N:25]([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH2:28][CH3:29].[OH2:34]>CS(C)=O>[C:2]([OH:1])(=[O:34])[C:15]([OH:17])=[O:18].[C:15]([OH:16])(=[O:18])[C:2]([OH:1])=[O:34].[CH2:30]([N:25]([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:24][CH2:23][CH2:22][O:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:6][CH:7]=1)[CH2:31][CH2:32][CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 96084N-(3-Chloropropyl)dibutylamineHCID 150806694-(pyridin-4-ylsulfanyl)phenol

Product 1

HCID 131716563HCID 131716563, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 0.014 mol of 4-(4-hydroxy-phenylthio)pyridine and 3 g of finely crushed anhydrous potassium carbonate in 50 ml of dimethylsulphoxide was placed under stirring for 30 min. To this medium 0.016 mol of 1-chloro-3-(di-n-butylamino)propane was added and the stirring was maintained at room-temperature for 24 hours. The reaction medium was poured into water and extracted with ethyl ether. The organic phase was washed with water, dried on sodium sulphate and filtered. After the solvent was evaporated off, an oil was provided which was purified by chromatography on a silica column (eluent:methanol). The required compound in free base form so obtained was then transformed into an oxalate by adding an ethereal solution of oxalic acid.

Workup

  1. temperaturethe stirring was maintained at room-temperature for 24 hours
  2. extractionextracted with ethyl ether
  3. washThe organic phase was washed with water
  4. customdried on sodium sulphate
  5. filtrationfiltered
  6. customAfter the solvent was evaporated off
  7. customan oil was provided which
  8. customwas purified by chromatography on a silica column (eluent:methanol)

Sources & evidence

ORD record
ord-f064c40c7ddc4526bb00d938568c5a1d
Source dataset
uspto-grants-1991_08
Patent number
US05039700

Reaction notes

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