4-Chlorobenzenesulfonyl chloride → HCID 14989646, compound

HRID 1199685Notes

Reaction equation

HRID 1199685 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[N:6][CH:7]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>N1C=CC=CC=1>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[N:6][CH:7]=2)(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 149896425-amino-2-Pyridinepropanoic acid

Product 1

HCID 14989646HCID 14989646, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-(5-aminopyrid-2-yl)propionic acid (1.00 g) and 4-chlorobenzenesulphonyl chloride (1.27 g) in pyridine (15 ml) was stirred at room temperature overnight. The solvent was removed and the residue was dissolved in dilute sodium hydroxide (30 ml) and extracted with chloroform (4×50 ml). The aqueous layer was acidified with dilute hydrochloric acid (pH 3) and extracted with ethyl acetate (4×100 ml). The ethyl acetate extracts were combined, dried over magnesium sulphate, the solvent was removed and the residue was recrystallised from acetonitrile to give the title compound (1.30 g). m.p. 144°-146° C.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in dilute sodium hydroxide (30 ml)
  3. extractionextracted with chloroform (4×50 ml)
  4. extractionextracted with ethyl acetate (4×100 ml)
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent was removed
  7. customthe residue was recrystallised from acetonitrile

Sources & evidence

ORD record
ord-8bbe9c805f954f44b1889cc6e7c4ff1d
Source dataset
uspto-grants-1990_02
Patent number
US04902698

Reaction notes

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