5-Aminovaleric acid hydrochloride → 5-(2,4,6-Trichloro-phenylsulfonamido)pentanoic acid

HRID 1642137Notes

Reaction equation

HRID 1642137 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[S:10](Cl)(=[O:12])=[O:11].Cl.[NH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21]>O1CCOCC1.[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[S:10]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])(=[O:12])=[O:11]

Participants

5

Reactant 2

HCID 693985-Aminovaleric acid hydrochlorideHCID 5213352,4,6-Trichlorobenzenesulfonyl chloride

Product 1

HCID 640607225-(2,4,6-Trichloro-phenylsulfonamido)pentanoic acid

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2,4,6-trichlorobenzenesulfonic acid chloride (3.00 g, 11 mmol) in 1,4-dioxane (50 ml) was added dropwise to a solution of 5-aminovaleric acid hydrochloride (1.50 g, 10 mmol) in 1 N sodium hydroxide solution (30 ml). The reaction mixture was stirred for 18 h at room temperature, and 1,4-dioxane was then distilled off in vacuo. The aqueous phase was extracted with ethyl acetate (3×50 ml) and then adjusted to pH 1 with concentrated hydrochloric acid. The acidic aqueous phase was extracted with ethyl acetate (3×60 ml). The combined organic phases were dried over sodium sulfate and concentrated in vacuo.

Workup

  1. distillation1,4-dioxane was then distilled off in vacuo
  2. extractionThe aqueous phase was extracted with ethyl acetate (3×50 ml)
  3. extractionThe acidic aqueous phase was extracted with ethyl acetate (3×60 ml)
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5c2db4ae97434ca8b71c000e270cba8f
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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