Sodium 3-nitrobenzenesulfonate → HCID 23176403, compound

HRID 893555Notes

Reaction equation

HRID 893555 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+].[Br-].[CH3:16][N+:17]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH3:27])[CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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].[CH3:27][N+:17]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH3:16])[CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 31389Sodium 3-nitrobenzenesulfonateHCID 23176407N-Benzyl-N,N-dimethyl-2-phenoxyethan-1-aminium bromide

Product 1

HCID 23176403HCID 23176403, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 22.52 grams (0.10 mol) of sodium m-nitrobenzenesulfonate in 100 milliters of water was added to a warm solution of 33.63 grams (0.10 mol) of N,N-dimethyl-N-(2-phenoxyethyl)benzylammonium bromide in 100 milliters of water. An oily precipitate formed which crystallized on standing. The solid was collected, washed with water and then with ether. The solid was dissolved in methylene chloride. The water layer was separated and the organic layer was dried over magnesium sulfate and concentrated to a solid. The solid was recrystallized from 2-butanone to give 32.5 grams (70.88% of theory) of product; mp=122°-124° C.

Workup

  1. customAn oily precipitate formed which
  2. customcrystallized
  3. customThe solid was collected
  4. washwashed with water
  5. dissolutionThe solid was dissolved in methylene chloride
  6. customThe water layer was separated
  7. dry with materialthe organic layer was dried over magnesium sulfate
  8. concentrationconcentrated to a solid
  9. customThe solid was recrystallized from 2-butanone
  10. customto give 32.5 grams (70.88% of theory) of product

Sources & evidence

ORD record
ord-efdf2a6843e647cda1340400ec62208b
Source dataset
uspto-grants-1992_06
Patent number
US05126225

Reaction notes

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