4-Chlorobenzenesulfonyl chloride → HCID 10476084, compound

HRID 2082570Notes

Reaction equation

HRID 2082570 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:7][CH:6]=1.C(N(CC)CC)C.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>C(Cl)Cl>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH:1][CH2:2][CH2:3][S:4][C:5]2[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:7][CH:6]=2)(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 9991247HCID 9991247, compound

Product 1

HCID 10476084HCID 10476084, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-[4-(2-aminoethylthio)phenyl]propionic acid (0.8 g), triethylamine (1.6 ml) and methylene chloride (50 ml) was added 4-chlorophenylsulfonyl chloride (0.79 g), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was washed successively with 3% hydrochloric acid and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. Evaporation of the solvent under reduced pressure gave a residue, which was then crystallized from ethyl acetate - n-hexane to give 3-{4-[2-(4-chlorophenylsulfonylamino)ethylthio]phenyl}propionic acid (Compound No. 52) (1.07 g).

Workup

  1. washThe reaction mixture was washed successively with 3% hydrochloric acid
  2. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  3. customEvaporation of the solvent under reduced pressure
  4. customgave a residue, which
  5. customwas then crystallized from ethyl acetate - n-hexane

Sources & evidence

ORD record
ord-2eda838d6ed045a496c1f0ca52933df9
Source dataset
uspto-grants-1993_02
Patent number
US05189211

Reaction notes

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