Ethanol → Ethyl 6-(p-chlorophenylsulfonamido)-2-[3-(3pyridyl)propyl]-hexanoate

HRID 465521Notes

Reaction equation

HRID 465521 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:20][CH2:21][CH2:22][C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[C:17]([OH:19])=[O:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH2:33](O)[CH3:34]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:20][CH2:21][CH2:22][C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[C:17]([O:19][CH2:33][CH3:34])=[O:18])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 149866366-(4-Chloro-benzenesulfonylamino)-2-(3-pyridin-3-yl-propyl)-hexanoic acid

Product 1

HCID 10004033Ethyl 6-(p-chlorophenylsulfonamido)-2-[3-(3pyridyl)propyl]-hexanoate

Procedure

To a solution of 2.53 g (5.9 mmol) of 6-(p-chlorophenylsulfonamido)-2-[3-(3-pyridyl)propyl]-hexanoic acid in 150 ml ethanol is slowly added 1.5 ml (20.5 mmol) thionyl chloride and the reaction mixture is subjected to reflux for 8 h. The solvent is evaporated and the residue is adjusted to pH 8 using 1N aqueous sodium hydroxide solution. The mixture is then extracted with methylene chloride (2×50 ml). Combined organic extracts are dried (MgSO4) and evaporated to give an oil which is then purified by flash chromatography using ether as the eluent to obtain ethyl 6-(p-chlorophenylsulfonamido)-2-[3-(3-pyridyl)propyl]-hexanoate as an oil.

Workup

  1. temperatureto reflux for 8 h
  2. customThe solvent is evaporated
  3. extractionThe mixture is then extracted with methylene chloride (2×50 ml)
  4. dry with materialCombined organic extracts are dried (MgSO4)
  5. customevaporated
  6. customto give an oil which
  7. customis then purified by flash chromatography

Sources & evidence

ORD record
ord-3b4a137c01b4401897d46b4c41f155e1
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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