Water → HCID 15413152, compound

HRID 1418831Notes

Reaction equation

HRID 1418831 reaction equation
[S:1]([CH2:5][CH2:6][CH2:7][NH:8][CH2:9][CH2:10][NH:11][CH2:12][CH2:13][CH2:14][S:15]([OH:18])(=[O:17])=[O:16])([OH:4])(=[O:3])=[O:2].[OH2:19].[OH-].[Na+:21].[C:22](Cl)(=[O:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>CC(C)=O>[C:22]([N:8]([CH2:9][CH2:10][N:11]([C:22](=[O:19])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:12][CH2:13][CH2:14][S:15]([O-:18])(=[O:16])=[O:17])[CH2:7][CH2:6][CH2:5][S:1]([O-:4])(=[O:2])=[O:3])(=[O:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].[Na+:21].[Na+:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8124Octanoyl chloride2×HCID 14798Sodium Hydroxide2×HCID 217084283,3′-(1,2-Ethanediyldiimino)bis[1-propanesulfonic acid]

Product 1

HCID 15413152HCID 15413152, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
10 °C

Procedure

Subsequently, N,N'-bis(3-sulfopropyl)ethylenediamine (5 g, 0.016 mol), water (30 g), and acetone (13 g) were placed in a four-necked flask. The pH of the contents was adjusted to 8.5 with an aqueous 4N NaOH solution. The flask was cooled to 10° C., and caprylic chloride (5.3 g, 0.033 mol) was added dropwise. Since pH falls as the reaction proceeds, an aqueous 4N NaOH solution was added if necessary to maintain the pH between 9 and 10. When the caprylic chloride had been completely added, the mixture was stirred for 1 hour. Water was removed using an evaporator while the mixture underwent azeotropic distillation with ethanol. Thereafter, water (250 g) was added and the mixture was filtered to remove insoluble matter. The residue was desalted by electrodialysis and then freeze-dried to obtain 3.0 g of disodium 4,7-dioctanoyl-4,7-diazadecane-1,10-disulfonate (separation yield: 31 wt %). Mass analysis (FAB ionization method) m/z: 601(M+H+), m=C24H46S2O8N2Na2.

Workup

  1. customSince pH falls as the reaction proceeds
  2. temperatureto maintain the pH between 9 and 10
  3. customWater was removed
  4. customan evaporator while the mixture
  5. distillationunderwent azeotropic distillation with ethanol
  6. additionThereafter, water (250 g) was added
  7. filtrationthe mixture was filtered
  8. customto remove insoluble matter
  9. customfreeze-dried

Sources & evidence

ORD record
ord-081a588c53ed4bde8ba0482361bb2abb
Source dataset
uspto-grants-1999_03
Patent number
US05885955

Reaction notes

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