Methane → Eprodisate Disodium

HRID 1740681Notes

Reaction equation

HRID 1740681 reaction equation
Br[CH2:2][CH2:3][CH2:4]Br.[S:6]([O-:9])([O-:8])=[O:7].[Na+:10].[Na+].C>O>[CH2:2]([S:6]([O-:9])(=[O:8])=[O:7])[CH2:3][CH2:4][S:6]([O-:9])(=[O:8])=[O:7].[Na+:10].[Na+:10]

Participants

5

Reactant 3

HCID 297MethaneHCID 80011,3-DibromopropaneHCID 24437Sodium Sulfite

Product 1

HCID 6451143Eprodisate DisodiumYield 85.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

This compound was prepared by a modification of the method described in Stone, G. C. H. (1936) J. Am. Chem. Soc., 58:488. 1,3-Dibromopropane (40.4 g, 0.20 mol) was treated with sodium sulfite (60.3 g, 0.50 mol) in water at reflux temperature for 48 h. Inorganic salts (sodium bromide and sodium sulfite) were removed by successive treatment of the resultant reaction mixture with barium hydroxide and silver(I)oxide. The solution was then neutralized with Amberlite-120 (acid form) and decolorized with Norit-A. Barium ions were removed by treatment of the aqueous solution with Amberlite-120 (sodium form) ion-exchange resin. The solvent was removed on a rotary evaporator, and the crude product was recrystallized from water-ethanol several times to give the title compound (42.5 g). The small amount of trapped ethanol was removed by dissolving the crystals in a minimum amount of water and then concentrating the solution to dryness. The pure product was further dried under high vacuum at 56° C. for 24 h: mp>300° C.; 1H NMR (D2O) δ:3.06-3.13 (m, 4H, H-1 and H-3), 2.13-2.29 (m, 2H, H-2); 13C NMR (D2O) δ:52.3 (C-1 and C-3), 23.8 (C-2).

Workup

  1. customThis compound was prepared by a modification of the method
  2. temperatureat reflux temperature for 48 h
  3. customInorganic salts (sodium bromide and sodium sulfite) were removed by successive treatment of the resultant
  4. customreaction mixture with barium hydroxide and silver(I)oxide
  5. customBarium ions were removed by treatment of the aqueous solution with Amberlite-120 (sodium form) ion-exchange resin
  6. customThe solvent was removed on a rotary evaporator
  7. customthe crude product was recrystallized from water-ethanol several times

Sources & evidence

ORD record
ord-96d63af3206542689be1ad306231b196
Source dataset
uspto-grants-1999_10
Patent number
US05972328

Reaction notes

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