5-Aminovaleric acid → 5-(4-Dimethylaminobenzenesulphonylamino)valeric acid

HRID 2248562Notes

Reaction equation

HRID 2248562 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[NH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20].[OH-].[Na+].O1CCCC1>O>[CH3:1][N:2]([CH3:13])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 1385-Aminovaleric acidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 125069434-(Dimethylamino)benzene-1-sulfonyl chloride

Product 1

HCID 117223405-(4-Dimethylaminobenzenesulphonylamino)valeric acidYield 61.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.4 g of 4-dimethylaminobenzenesulphonyl chloride (Chem. Ber. 43, 3038, (1910)) are added to a solution comprising 2.34 g of 5-aminovaleric acid and 2.4 g of sodium hydroxide dissolved in 24 cm3 of water, followed by the addition of 24 cm3 of tetrahydrofuran in order to obtain a solution. The temperature rises to 36° C. The mixture is kept stirring for 4 hours, the tetrahydrofuran is evaporated off, the reaction medium is acidified using acetic acid and extracted with chloroform, the organic phase is dried and the solvents are removed under reduced pressure. 3.7 g of expected product are obtained. M.p. 105°-110° C. After crystallization in an isopropanol/water mixture (1:1), the product, melting point 118°-120° C., is obtained.

Workup

  1. customto obtain a solution
  2. customrises to 36° C
  3. customthe tetrahydrofuran is evaporated off
  4. extractionextracted with chloroform
  5. customthe organic phase is dried
  6. customthe solvents are removed under reduced pressure

Sources & evidence

ORD record
ord-7b7cea8af58a4877bb955a8a5c20c01d
Source dataset
uspto-grants-1991_08
Patent number
US05041436

Reaction notes

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