Diphenyl disulfide → 4-[(4-Sulfophenyl)disulfanyl]benzenesulfonic acid

HRID 351023

Reaction equation

HRID 351023 reaction equation
[C:1]1([S:7][S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[S:16]([OH:19])(=[O:18])=[O:17]>ClCCl>[C:12]1([S:16]([OH:19])(=[O:18])=[O:17])[CH:13]=[CH:14][C:9]([S:8][S:7][C:1]2[CH:2]=[CH:3][C:4]([S:16]([OH:19])(=[O:18])=[O:17])=[CH:5][CH:6]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 13436Diphenyl disulfideHCID 24638Chlorosulfonic acid

Product 1

HCID 3859544-[(4-Sulfophenyl)disulfanyl]benzenesulfonic acidYield 79.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of phenyl disulfide (4.36 g, 20 mmol) in dichloromethane (40 mL) at 0° C. is added a solution of chlorosulfonic acid (4.64 g, 2.95 mL, 40 mmol) in dichloromethane (60 mL) dropwise. The mixture is stirred at 0° C. for 1 hour followed by 1.5 hours at room temperature. The reaction mixture is concentrated to dryness in vacuo and the residue is partitioned between diethyl ether and water. The water phase is separated, made basic with 2N aqueous sodium hydroxide and concentrated in vacuo to half the volume. The resulting solution is refrigerated overnight. The precipitate formed overnight is discarded, the filtrate is concentrated further in vacuo until a solid started to appear. The mixture is placed in the refrigerator for 2 hours. The mixture is treated with ethanol, the solid formed is filtered, washed with ethanol twice and dried under high vacuum overnight at room temperature to give 6.0 g of 4,4′-dithiobisbenzenesulfonic acid as a white solid: [M−1]−=398.8.

Workup

  1. waitfollowed by 1.5 hours at room temperature
  2. concentrationThe reaction mixture is concentrated to dryness in vacuo
  3. customthe residue is partitioned between diethyl ether and water
  4. customThe water phase is separated
  5. concentrationconcentrated in vacuo to half the volume
  6. waitThe resulting solution is refrigerated overnight
  7. customThe precipitate formed overnight
  8. concentrationthe filtrate is concentrated further in vacuo until a solid
  9. waitThe mixture is placed in the refrigerator for 2 hours
  10. additionThe mixture is treated with ethanol
  11. customthe solid formed
  12. filtrationis filtered
  13. washwashed with ethanol twice
  14. customdried under high vacuum overnight at room temperature

Sources & evidence

ORD record
ord-de02f5b7f4f9441383bb33967f59cfaf
Source dataset
uspto-grants-2007_02
Patent number
US07183304B2

Linked notes

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