5-Aminovaleric acid → HCID 19815887, compound

HRID 2247826Notes

Reaction equation

HRID 2247826 reaction equation
[CH2:1]([N:3]([CH2:14][CH3:15])[C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)[CH3:2].N[CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22].[OH-].[Na+].O1CCCC1>O>[CH2:1]([N:3]([CH2:14][CH3:15])[C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])(=[O:12])=[O:11])=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 1385-Aminovaleric acidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 198110054-(Diethylamino)benzenesulfonyl chloride

Product 1

HCID 19815887HCID 19815887, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.5 g of 4-diethylaminobenzenesulphonyl chloride are added to a solution comprising 1.17 g of 5-aminovaleric acid and 1.2 g of sodium hydroxide dissolved in 12 cm3 of water, followed by the addition of 12 cm3 of tetrahydrofuran in order to obtain a solution. The mixture is kept stirring for 2 hours at room temperature, 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. 2.2 g of expected product are obtained. M.p. 106°-108° C. After crystallization in an isopropanol/water mixture (1:1), the product, melting point 109°-110° C., is obtained.

Workup

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

Sources & evidence

ORD record
ord-bab02705074e4763938f2f5bba084a0e
Source dataset
uspto-grants-1991_08
Patent number
US05037822

Reaction notes

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