Sodium 3-nitrobenzenesulfonate → N-(2-(Benzoyloxy)ethyl)-N,N-dimethyl-n-octadecylammonium m-nitrobenzenesulfonate

HRID 1613702Notes

Reaction equation

HRID 1613702 reaction equation
[Br-].[C:2]([O:10][CH2:11][CH2:12][N+:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])([CH3:15])[CH3:14])(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N+:34]([C:37]1[CH:38]=[C:39]([S:43]([O-:46])(=[O:45])=[O:44])[CH:40]=[CH:41][CH:42]=1)([O-:36])=[O:35].[Na+]>O>[N+:34]([C:37]1[CH:38]=[C:39]([S:43]([O-:46])(=[O:44])=[O:45])[CH:40]=[CH:41][CH:42]=1)([O-:36])=[O:35].[C:2]([O:10][CH2:11][CH2:12][N+:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])([CH3:14])[CH3:15])(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 31389Sodium 3-nitrobenzenesulfonateHCID 19774320N-(2-(Benzoyloxy)ethyl)-N,N-dimethyl-n-octadecylammonium bromide

Product 1

HCID 19774327N-(2-(Benzoyloxy)ethyl)-N,N-dimethyl-n-octadecylammonium m-nitrobenzenesulfonateYield 66.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 26.33 g (0.05 mol) of N-(2-(benzoyloxy)ethyl)-N,N-dimethyl-n-octadecylammonium bromide (prepared as described in Example 36) dissolved in 500 ml of water at 70° C. was added a solution of 11.26 g (0.05 mol) of sodium m-nitrobenzenesulfonate in 100 ml of water. The resultant mixture was extracted with methylene chloride. The water layer was separated and the organic layer was dried over MgSO4 and concentrated. The solid was recrystallized from ethyl acetate, collected, washed with ligroine, and dried to yield 21.7 g of the title compound; mp=80°-3° C. ##STR26##

Workup

  1. extractionThe resultant mixture was extracted with methylene chloride
  2. customThe water layer was separated
  3. dry with materialthe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe solid was recrystallized from ethyl acetate
  6. customcollected
  7. washwashed with ligroine
  8. customdried

Sources & evidence

ORD record
ord-9e4c88b4b7104584871baa5310561e0d
Source dataset
uspto-grants-1993_03
Patent number
US05194472

Reaction notes

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