Triethylamine → Triethylammonium 2-mercaptobenzenesulfonate

HRID 867967Notes

Reaction equation

HRID 867967 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([O-:11])(=[O:10])=[O:9].[NH3+]C1C=CC=CC=1.[CH2:19]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[CH3:20]>>[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([O-:11])(=[O:10])=[O:9].[CH2:19]([NH+:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[CH3:20]

Participants

3

Reactant 2

HCID 8471TriethylamineHCID 21289555Anilinium 2-mercaptobenzenesulfonate

Product 1

HCID 21289563Triethylammonium 2-mercaptobenzenesulfonateYield 50.3%

Procedure

Then, 2.0 g of the resulting anilinium 2-mercaptobenzenesulfonate was subjected to ion-exchange column chromatography (about 30 ml of Dowex 50W-X2, 100-200 mesh, H-form was filled into a column) and eluted with a mixed solvent of methanol and water (4/1, v/v). Acidic fractions were concentrated under reduced pressure, and about 50 ml of isopropanol was added to the resulting syrup. The solvent was evaporated under reduced pressure. To 1.1 g of the resulting syrup, about 4 ml of isopropanol was added to form a solution. Triethylamine (0.58 g) was added to the solution, and the resulting crystals were collected by filtration to give 0.84 g of the captioned compound as colorless crystals (melting point: 89° to 90° C.)

Workup

  1. additionwas filled into a column) and
  2. washeluted with a mixed solvent of methanol and water (4/1
  3. concentrationAcidic fractions were concentrated under reduced pressure, and about 50 ml of isopropanol
  4. additionwas added to the resulting syrup
  5. customThe solvent was evaporated under reduced pressure
  6. additionTo 1.1 g of the resulting syrup, about 4 ml of isopropanol was added
  7. customto form a solution
  8. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-748b44393511451da0101d6c8f5f41a5
Source dataset
uspto-grants-1988_10
Patent number
US04777267

Reaction notes

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