5-Aminovaleric acid → HCID 19994509, compound

HRID 2248566Notes

Reaction equation

HRID 2248566 reaction equation
[CH2:1]([N:4]([CH2:15][CH2:16][CH3:17])[C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)[CH2:2][CH3:3].[NH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24].[OH-].[Na+].O1CCCC1>O>[CH2:1]([N:4]([CH2:15][CH2:16][CH3:17])[C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])(=[O:13])=[O:12])=[CH:7][CH:6]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 1385-Aminovaleric acidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 199945044-(Dipropylamino)benzenesulfonyl chloride

Product 1

HCID 19994509HCID 19994509, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6.5 g of 4-dipropylaminobenzenesulphonyl chloride, in solution, are added to a solution comprising 2.76 g of 5-aminovaleric acid and 2.82 g of sodium hydroxide dissolved in 28 cm3 of water, followed by the addition of 28 cm3 of tetrahydrofuran. The mixture is kept stirring for 2 hours, the tetrahydrofuran is evaporated off, the reaction medium is acidified using acetic acid and the solid formed is filtered off, washed with water and dried. 6 g of expected product are obtained. M.p. 95°-98° C. After crystallization in an isopropanol/water mixture (1:1), 5 g of product, melting point 98°-99° C., are obtained.

Workup

  1. customthe tetrahydrofuran is evaporated off
  2. customthe solid formed
  3. filtrationis filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-088f68b1c6e5489881b846608fdadc39
Source dataset
uspto-grants-1991_08
Patent number
US05041436

Reaction notes

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