Water → HCID 19759158, compound

HRID 2051213Notes

Reaction equation

HRID 2051213 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:17](=[O:20])([O-:19])[O-].[K+].[K+].Cl[CH2:24][CH2:25][CH2:26][N:27]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH2:30][CH3:31].[OH2:36]>CS(C)=O>[C:2]([OH:1])(=[O:36])[C:17]([OH:19])=[O:20].[CH2:32]([N:27]([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:26][CH2:25][CH2:24][O:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1)[CH2:33][CH2:34][CH3:35]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 96084N-(3-Chloropropyl)dibutylamineHCID 19759090HCID 19759090, compound

Product 1

HCID 19759158HCID 19759158, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 0.0085 mol of 2-(4-hydroxy-benzenesulphonyl)pyridine in 50 ml of dimethylsulphoxide, were added 3 g of finely crushed anhydrous potassium carbonate. The mixture was then maintained under stirring for 30 min and 0.015 mol of 1-chloro-3-(di-n-butylamino)propane was added. Stirring was still maintained for 24 hours and the reaction mixture was then poured into water and extracted with ethyl ether. The organic layer was washed with water, dried on sodium sulphate and filtered. After the filtrate was evaporated, the desired product so obtained was purified by chromatography on a silica column using methanol as eluent. The pure base so obtained was then transformed into an oxalate by addition of oxalic acid in ethyl ether.

Workup

  1. temperatureThe mixture was then maintained
  2. stirringStirring
  3. temperaturewas still maintained for 24 hours
  4. extractionextracted with ethyl ether
  5. washThe organic layer was washed with water
  6. customdried on sodium sulphate
  7. filtrationfiltered
  8. customAfter the filtrate was evaporated

Sources & evidence

ORD record
ord-a4252992bfae485fbeac3c3ea46a4927
Source dataset
uspto-grants-1991_05
Patent number
US05017579

Reaction notes

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