Aniline → HCID 22416098, compound

HRID 1440871Notes

Reaction equation

HRID 1440871 reaction equation
[CH2:1]1[S:6](=[O:8])(=[O:7])[O:5][CH2:4][CH2:3][CH2:2]1.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C>[NH:9]([CH2:4][CH2:3][CH2:2][CH2:1][S:6]([OH:5])(=[O:8])=[O:7])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 154111,4-Butane sultone

Product 1

HCID 22416098HCID 22416098, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of butanesultone (27.2 g, 0.2 mol) and aniline (46.5 g, 0.5 mol) in ethanol is heated under reflux for 4 hr. and cooled to room temperature to precipitate a white solid. The precipitates are filtered and recrystallized in ethanol to obtain 4-anilino-1-butanesulfonic acid (42.2 g, 90%) as white crystals. 4-Anilino-1-butanesulfonic acid (10 g) is dissolved in water and neutralized by sodium hydroxide. The neutral solution is concentrated under reduced pressure to give white solids. The solids are crystallized in methanol-chloroform to obtain 4-anilino-1-butanesulfonic acid sodium salt (10.0 g, 92%) as white crystals.

Workup

  1. temperatureunder reflux for 4 hr
  2. customto precipitate a white solid
  3. filtrationThe precipitates are filtered
  4. customrecrystallized in ethanol

Sources & evidence

ORD record
ord-0cd4fd46a6664eea9c6bf0ec7b9b9ec4
Source dataset
uspto-grants-1996_03
Patent number
US05500474

Reaction notes

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