Sodium 3-nitrobenzenesulfonate → N,N-Dimethyl-N-(2-benzoylaminoethyl)benzylammonium m-Nitrobenzenesulfonate

HRID 372940

Reaction equation

HRID 372940 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([O-:13])(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Na+].[Cl-].[CH3:16][N+:17]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([CH3:29])[CH2:18][CH2:19][NH:20][C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([O-:13])(=[O:11])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:29][N+:17]([CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)([CH3:16])[CH2:18][CH2:19][NH:20][C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 31389Sodium 3-nitrobenzenesulfonateHCID 19811098N,N-Dimethyl-N-(2-benzoylaminoethyl)benzylammonium Chloride

Product 1

HCID 86746309N,N-Dimethyl-N-(2-benzoylaminoethyl)benzylammonium m-Nitrobenzenesulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 11.26 grams (0.05 mol) of sodium m-nitrobenzenesulfonate in 50 milliters of water was added to a solution of 15.94 grams (0.05 mol) of the N,N-dimethyl-N-(2-benzoylaminoethyl)benzylammonium chloride, prepared as described in Example 2, in 50 milliters of water. An oily precipitate formed. The water layer was decanted and the oil was rinsed with water, dissolved in methylene chloride, dried over magnesium sulfate and concentrated to a viscous oil. The oil was treated with ligroine (bp=35°-60° C.) with warming. The oil crystallized and the solid formed was collected and recrystallized from isopropanol. The yield of product was 10.75 grams (44.28% of theory); mp=109°-112° C.

Workup

  1. customprepared
  2. customAn oily precipitate formed
  3. customThe water layer was decanted
  4. washthe oil was rinsed with water
  5. dissolutiondissolved in methylene chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to a viscous oil
  8. additionThe oil was treated with ligroine (bp=35°-60° C.)
  9. temperaturewith warming
  10. customThe oil crystallized
  11. customthe solid formed
  12. customwas collected
  13. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-1306be5017d14878b275a1dd2041354e
Source dataset
uspto-grants-1992_11
Patent number
US05162188

Linked notes

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