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

HRID 358625Notes

Reaction equation

HRID 358625 reaction equation
[NH2:1][CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].[OH-].[Na+].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>O.C(Cl)(Cl)Cl>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH:1][CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 86744642(Z)-7-Aminohept-5-enoic Acid

Product 1

HCID 67946824(Z)-7-(4-Chlorobenzenesulphonamido)hept-5-enoic AcidYield 29.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A rapidly stirred solution of (Z)-7-aminohept-5-enoic acid (0.61 g), sodium hydroxide (0.51 g) in water (5 ml) was treated with 4-chlorobenzenesulphonyl chloride (0.9 g) in chloroform (2.5 ml). The solution was stirred for 24 hours then evaporated with chloroform (4×15 ml). The aqueous layer was treated with hydrochloric acid to pH=1 and extracted with chloroform (4×40 ml). These chloroform extracts were combined, dried over magnesium sulphate and evaporated to dryness. The residue was recrystallised from isopropanol to give the title compound (0.4 g). N.M.R; 250 MHz; δ(CDCl3) (ppm): 1.7 (m, 2H) 2.05 (m, 2H), 2.35 (m, 2H), 3.6 (t, 2H), 4.9 (t, 1H) 5.3 (m, 1H), 5.45 (m, 1H) 7.45 (m, 2H), 7.8 (m, 2H).

Workup

  1. customthen evaporated with chloroform (4×15 ml)
  2. additionThe aqueous layer was treated with hydrochloric acid to pH=1
  3. extractionextracted with chloroform (4×40 ml)
  4. dry with materialdried over magnesium sulphate
  5. customevaporated to dryness
  6. customThe residue was recrystallised from isopropanol

Sources & evidence

ORD record
ord-1e7c61b2f8b548c9a1638b4074d2b5d2
Source dataset
uspto-grants-1991_03
Patent number
US04997847

Reaction notes

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