Water → N-(4-methoxybutyl)benzene-1,2-diamine

HRID 2168889Notes

Reaction equation

HRID 2168889 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].CS(O[CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH3:19])(=O)=O.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH3:19][O:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:7][C:2]1[C:1]([NH2:8])=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7243O-PhenylenediamineHCID 11430Potassium CarbonateHCID 116870064-Methoxybutyl methanesulfonate

Product 1

HCID 58355733N-(4-methoxybutyl)benzene-1,2-diamineYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of phenylenediamine (10.8 g) and 4-methoxybutyl methanesulfonate (9.11 g) in acetonitrile (100 ml) was added potassium carbonate (20.7 g), and the mixture was stirred heated under reflux for 15 hr. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (35:65) was concentrated under reduced pressure to give the object product (5.44 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 15 hr
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. washa fraction eluted with ethyl acetate-hexane (35:65)
  8. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-c528da77a0e541418a97f89a42910977
Source dataset
uspto-grants-2015_06
Patent number
US09045436B2

Reaction notes

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