Hydrochloric Acid → 3,3'-(Ethane-1,2-diyldisulfanediyl)di(propane-1-sulfonic acid)

HRID 874058Notes

Reaction equation

HRID 874058 reaction equation
[Na+].Br[CH2:3][CH2:4][CH2:5][S:6]([O-:9])(=[O:8])=[O:7].C[O-].[Na+].[CH2:13]([SH:16])[CH2:14][SH:15].Cl>CCO.O>[CH2:13]([S:16][CH2:3][CH2:4][CH2:5][S:6]([OH:9])(=[O:8])=[O:7])[CH2:14][S:15][CH2:3][CH2:4][CH2:5][S:6]([OH:9])(=[O:8])=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 109021,2-EthanedithiolHCID 10942334Sodium MethoxideHCID 236790563-bromopropanesulfonic acid sodium salt

Product 1

HCID 123464103,3'-(Ethane-1,2-diyldisulfanediyl)di(propane-1-sulfonic acid)

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 3-bromopropane sulfonic acid sodium salt (24.7 g, 110 mmol) and sodium methoxide (7.06 g, 131 mmol) in EtOH (300 mL) at ambient temperature was added, dropwise, 1,2-ethanedithiol (4.4 mL, 52.3 mmol) in ethanol (25 mL). Allowed to stir at room temperature for one hour, and then heated to reflux overnight. Cooled to room temperature and acidified with 2 N HCl to pH 1-2. The resulting suspension was heated to 75° C. and water was slowly added in small portions until a clear solution was obtained. Cooled to room temperature, and then to 5° C. The resulting white precipitate was filtered off, washed with cold EtOH and dried, giving 11.9 g (67.4%) as a white powder. 1H NMR (400 MHz, D2O) δ 3.10 (t, J=7.2 Hz, 4H), 2.92 (s, 4H), 2.82 (t, J=7.2 Hz, 4H), 2.11 (m, 4H). 13C NMR (101 MHz, D2O) δ 52.26, 33.38, 32.27, 26.80.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. temperatureCooled to room temperature
  4. temperatureThe resulting suspension was heated to 75° C.
  5. customwas obtained
  6. temperatureCooled to room temperature
  7. customto 5° C
  8. filtrationThe resulting white precipitate was filtered off
  9. washwashed with cold EtOH
  10. customdried
  11. customgiving 11.9 g (67.4%) as a white powder

Sources & evidence

ORD record
ord-c355248fa4934277899ab2434470b680
Source dataset
uspto-grants-2015_03
Patent number
US08980077B2

Reaction notes

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