Reaction #324356

ord-ea36cede2a55439582f41fdf9e0414d9

Reaction equation

Nc1ccccc1
aniline
CCN(C(C)C)C(C)C
N,N-diisopropylethylamine
O=S1(=O)CCCO1
propane sultone
→
CC[NH+](C(C)C)C(C)C.CC[NH+](C(C)C)C(C)C.O=S(=O)([O-])CCCN(CCCS(=O)(=O)[O-])c1ccccc1
di[ethyl(diisopropyl)ammonium] 3-(3-sulfonatopropylanilino)-1-propanesulfonate
Yield 94.0%

Reactants

Nc1ccccc1
aniline
CCN(C(C)C)C(C)C
N,N-diisopropylethylamine
O=S1(=O)CCCO1
propane sultone

Reagents

None

Solvents

CC#N
acetonitrile

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe solvent was evaporated
  2. 2
    workup.ADDITIONethylacetate was added
  3. 3
    FiltrationThe precipitated DIPEA bromide was filtered off
  4. 4
    Otherthe filtrate was evaporated
  5. 5
    workup.ADDITIONThe residue was treated with ether

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%.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08642014B2uspto-grants-2014_02