4-Chlorobenzenesulfonyl chloride → 7-(4-Chlorobenzenesulphonamido)hept-5-ynoic Acid

HRID 358621Notes

Reaction equation

HRID 358621 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][C:14]#[C:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20].[OH-].[Na+]>C(Cl)(Cl)Cl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][CH2:13][C:14]#[C:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 200669627-Aminohept-5-ynoic Acid

Product 1

HCID 200669707-(4-Chlorobenzenesulphonamido)hept-5-ynoic AcidYield 19%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

4-Chlorobenzenesulphonyl chloride (0.31 g) in chloroform (2 ml) was added to a rapidly stirred solution of 7-aminohept-5-ynoic acid (0.2 g) and sodium hydroxide (0.21 g) in water (3 ml) and stirring was continued for 24 hours. The solution was extracted with chloroform (4×10 ml). The remaining aqueous layer was cooled, treated with hydrochloric acid and the resulting precipitate was collected by filtration and recrystallised from isopropanol-water to give the title compound (0.085 g). m.p. 91°-93° C.

Workup

  1. extractionThe solution was extracted with chloroform (4×10 ml)
  2. temperatureThe remaining aqueous layer was cooled
  3. additiontreated with hydrochloric acid
  4. filtrationthe resulting precipitate was collected by filtration
  5. customrecrystallised from isopropanol-water

Sources & evidence

ORD record
ord-70ab447eef6349e3b86494f02395014e
Source dataset
uspto-grants-1991_03
Patent number
US04997847

Reaction notes

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