Sodium 3-nitrobenzenesulfonate → HCID 86745755, compound

HRID 1613694Notes

Reaction equation

HRID 1613694 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-].[C:16]([O:24][CH2:25][CH2:26][N+:27]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([CH3:29])[CH3:28])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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].[C:16]([O:24][CH2:25][CH2:26][N+:27]([CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)([CH3:29])[CH3:28])(=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 31389Sodium 3-nitrobenzenesulfonateHCID 15611848HCID 15611848, compound

Product 1

HCID 86745755HCID 86745755, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 45.03 g (0.20 mol) of sodium m-nitrobenzenesulfonate in 200 ml of water was added to a solution of 63.97 g (0.20 mol) of N-(2-(benzoyloxy)ethyl)-N,N-dimethylbenzylammonium chloride (prepared as described in Example 9) in 250 ml of water. An oily precipitate immediately formed. The water was decanted from the oil and fresh water was added. After standing overnight, the oil was taken up in methylene chloride. The water layer was separated and the organic layer was dried over MgSO4 and concentrated to an oil which crystallized on treatment with ether. The solid was collected, recrystallized from 2-butanone, collected, washed with ether and dried. The yield of product was 36.0 g; mp=104°-6° C.

Workup

  1. customAn oily precipitate immediately formed
  2. customThe water was decanted from the oil and fresh water
  3. additionwas added
  4. customThe water layer was separated
  5. dry with materialthe organic layer was dried over MgSO4
  6. concentrationconcentrated to an oil which
  7. customcrystallized on treatment with ether
  8. customThe solid was collected
  9. customrecrystallized from 2-butanone
  10. customcollected
  11. washwashed with ether
  12. customdried

Sources & evidence

ORD record
ord-1a9ec7813116449db2e8c94c6948a655
Source dataset
uspto-grants-1993_03
Patent number
US05194472

Reaction notes

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