Aniline → Di[ethyl(diisopropyl)ammonium] 3-(3-sulfonatopropylanilino)-1-propanesulfonate

HRID 237174

Reaction equation

HRID 237174 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:8]([N:11]([CH2:15][CH3:16])[CH:12]([CH3:14])[CH3:13])([CH3:10])[CH3:9].[CH2:17]1[S:21](=[O:23])(=[O:22])[O:20][CH2:19][CH2:18]1>C(#N)C>[S:21]([CH2:17][CH2:18][CH2:19][N:1]([CH2:14][CH2:12][CH2:13][S:21]([O-:23])(=[O:22])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([O-:20])(=[O:23])=[O:22].[CH2:15]([NH+:11]([CH:12]([CH3:14])[CH3:13])[CH:8]([CH3:10])[CH3:9])[CH3:16].[CH2:17]([NH+:1]([CH:2]([CH3:3])[CH3:7])[CH:8]([CH3:10])[CH3:9])[CH3:18]

Participants

5

Reactant 3

HCID 6115AnilineHCID 14264Propane sultoneHCID 81531Diisopropylethylamine

Product 1

HCID 86646640Di[ethyl(diisopropyl)ammonium] 3-(3-sulfonatopropylanilino)-1-propanesulfonateYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of aniline (7 mmol), N,N-diisopropylethylamine (DIPEA, 18 mmol) and propane sultone (16 mmol) was heated in a pressure tube in 10 mL of acetonitrile at 120-130° C. for 9 h under argon atmosphere. The solvent was evaporated and ethylacetate was added. The precipitated DIPEA bromide was filtered off and the filtrate was evaporated. The residue was treated with ether to give di[ethyl(diisopropyl)ammonium] 3-(3-sulfonatopropylanilino)-1-propanesulfonate as a white or pinky-white solid. Yield: 94%.

Workup

  1. customThe solvent was evaporated
  2. additionethylacetate was added
  3. filtrationThe precipitated DIPEA bromide was filtered off
  4. customthe filtrate was evaporated
  5. additionThe residue was treated with ether

Sources & evidence

ORD record
ord-ea36cede2a55439582f41fdf9e0414d9
Source dataset
uspto-grants-2014_02
Patent number
US08642014B2

Linked notes

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