4-Chlorobenzenesulfonyl chloride → 8-(4-Chlorobenzenesulphonamido)-octanoic acid

HRID 358609

Reaction equation

HRID 358609 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21]>C(Cl)(Cl)Cl.[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 660858-Aminooctanoic acid

Product 1

HCID 200669408-(4-Chlorobenzenesulphonamido)-octanoic acidYield 60.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4-chlorobenzenesulphonyl chloride (6 mmol) in chloroform (2.5 ml) was added to a solution of 8-aminooctanoic acid (6 mmol) in 10% sodium hydroxide solution (10 ml). The mixture was stirred at room temperature for 24 hours and was then extracted with chloroform (4×40 ml), the chloroform layers being discarded. The aqueous layer was acidified to pH1 with conc. HCl and was extracted with chloroform (4×100 ml). The combined chloroform extracts were then dried (Mg SO4). Concentration and crystallisation from isopropanol-water gave 8-(4-chlorobenzenesulphonamido)-octanoic acid (1.22 g; 58%); m.p. 122°-124° C.

Workup

  1. extractionwas then extracted with chloroform (4×40 ml)
  2. extractionwas extracted with chloroform (4×100 ml)
  3. dry with materialThe combined chloroform extracts were then dried (Mg SO4)
  4. concentrationConcentration and crystallisation from isopropanol-water

Sources & evidence

ORD record
ord-1cbdab5e0d8143c8b8e925b1458b9241
Source dataset
uspto-grants-1991_03
Patent number
US04997847

Linked notes

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