Sodium hydrosulfide hydrate → Sodium 2-hydroxy-3-sulfanylpropane-1-sulfonate

HRID 1275416Notes

Reaction equation

HRID 1275416 reaction equation
O.Cl[CH2:3][CH:4]([OH:10])[CH2:5][S:6]([O-:9])(=[O:8])=[O:7].[Na+:11].O.[SH-:13].[Na+]>CN(C=O)C>[SH:13][CH2:3][CH:4]([OH:10])[CH2:5][S:6]([O-:9])(=[O:8])=[O:7].[Na+:11]

Participants

4

Reactant 2

HCID 16211346Sodium hydrosulfide hydrateHCID 23665651Sodium 3-chloro-2-hydroxypropane-1-sulfonate--water (1/1/1)

Product 1

HCID 23663670Sodium 2-hydroxy-3-sulfanylpropane-1-sulfonateYield 172.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To sodium 3-chloro-2-hydroxypropanesulfonate hydrate (2.0 g), sodium hydrosulfide hydrate (0.42 g) was added in 10 mL DMF. The mixture was refluxed overnight. When the reaction mixture was cooled down, white solid was isolated, rinsed with ether and acetone to obtain 1.9 g crude sodium 3-mercapto-2-hydroxypropane sulfonate. The crude product was dissolved in water and preferentially precipitated the desired product by adding acetone. The precipitated product was then filtered and dried under vacuum to get 1.04 g of the title compound.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. temperatureWhen the reaction mixture was cooled down
  3. customwhite solid was isolated
  4. washrinsed with ether and acetone

Sources & evidence

ORD record
ord-dba88060dfeb4f4c8d98aa631c8a672c
Source dataset
uspto-grants-2000_12
Patent number
US06160167

Reaction notes

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