Sodium 3-nitrobenzenesulfonate → N-(4-Methylvaleryloxyethyl)-N,N-dimethylbenzylammonium m-nitrobenzenesulfonate

HRID 1613693Notes

Reaction equation

HRID 1613693 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][CH:17]([CH3:35])[CH2:18][CH2:19][C:20]([O:22][CH2:23][CH2:24][N+:25]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH3:27])[CH3:26])=[O:21]>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].[CH3:16][CH:17]([CH3:35])[CH2:18][CH2:19][C:20]([O:22][CH2:23][CH2:24][N+:25]([CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)([CH3:26])[CH3:27])=[O:21]

Participants

4

Reactant 2

HCID 31389Sodium 3-nitrobenzenesulfonateHCID 86745753N-(4-Methylvaleryloxyethyl)-N,N-dimethylbenzylammonium chloride

Product 1

HCID 86745754N-(4-Methylvaleryloxyethyl)-N,N-dimethylbenzylammonium m-nitrobenzenesulfonateYield 67.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A hot solution (300 ml) of 56.29 g (0.25 mol) of sodium m-nitrobenzenesulfonate in water was added to a solution (300 ml) of 78.48 g (0.25 mol) of N-(2-(4-methylvaleryloxy)ethyl)-N,N-dimethylbenzylammonium chloride (prepared as described in Example 8) in water. An oily precipitate formed immediately which crystallized on cooling. The solid was collected, washed with water and dissolved in methylene chloride. The water layer was separated and the organic layer was dried over MgSO4 and concentrated. Recrystallization of the solid residue from isopropanol gave 81.6 g of product; mp=106°-8° C.

Workup

  1. customAn oily precipitate formed immediately which
  2. customcrystallized
  3. temperatureon cooling
  4. customThe solid was collected
  5. washwashed with water
  6. dissolutiondissolved in methylene chloride
  7. customThe water layer was separated
  8. dry with materialthe organic layer was dried over MgSO4
  9. concentrationconcentrated
  10. customRecrystallization of the solid residue from isopropanol

Sources & evidence

ORD record
ord-e92d3318ff884038b0d8a79aa0f445c9
Source dataset
uspto-grants-1993_03
Patent number
US05194472

Reaction notes

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