Aniline → HCID 88392765, compound

HRID 1440870Notes

Reaction equation

HRID 1440870 reaction equation
[Na+:1].Br[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8]([O-:11])(=[O:10])=[O:9].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)(O)[O-].[K+]>O>[Na+:1].[NH:12]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8]([O-:11])(=[O:10])=[O:9])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 516893Potassium BicarbonateHCID 236678325-Bromo-1-pentanesulfonic Acid Sodium Salt

Product 1

HCID 88392765HCID 88392765, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture is washed with ether and the aqueous layer is concentrated to give white solids. The solids are dissolved in ethanol with heating, and cooled slowly to room temperature to precipitate sodium bromide. The precipitates are filtered off and the filtrate is put in a refrigerator overnight to obtain 5-bromo-t-pentanesulfonic acid sodium salt (12.9 g, 68%) as white crystals. A solution of 5-bromo-1-pentanesulfonic acid sodium salt (12.9 g, 0.05 mol) and aniline (20 g, 0.22 mol) in water (150 mL) is heated under reflux with potassium bicarbonate (6.3 g, 0.075 mol) for 8 hr. After the reaction is completed, the reaction mixture is washed with ether and the aqueous layer is concentrated to give white solids. The solid is recrystallized in methanol to obtain 5-anilino-1-pentanesulfonic acid sodium salt (10.6 g, 80%) as white crystals.

Workup

  1. washthe reaction mixture is washed with ether
  2. concentrationthe aqueous layer is concentrated
  3. customto give white solids
  4. customThe solid is recrystallized in methanol

Sources & evidence

ORD record
ord-d82500c1f0254265b2d76d9669c60791
Source dataset
uspto-grants-1996_03
Patent number
US05500474

Reaction notes

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