Water → N-(2-Benzoyloxyethyl)pyridinium m-Nitrobenzenesulfonate

HRID 248792

Reaction equation

HRID 248792 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+].O.[Br-].[C:17]([O:25][CH2:26][CH2:27][N+:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[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:17]([O:25][CH2:26][CH2:27][N+:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 31389Sodium 3-nitrobenzenesulfonateHCID 19762119N-(2-benzoyloxyethyl)pyridinium bromide

Product 1

HCID 19762115N-(2-Benzoyloxyethyl)pyridinium m-Nitrobenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 15.41 grams (0.05 mole) of N-(2-benzoyloxyethyl)pyridinium bromide, prepared as described in Example 2, in 50 milliters of water. The resultant solution was treated with methylene chloride resulting in the formation of three layers. The center layer was isolated, treated with ligroine (bp=70°-90° C.) and allowed to stand with spatula scratching of the oil. Crystallization occurred and the solid was collected, washed with ether and recrystallized from acetonitrile. The yield of product was 6.6 grams (30.67% of theory); mp=128°-130° C.

Workup

  1. customprepared
  2. customThe center layer was isolated
  3. additiontreated with ligroine (bp=70°-90° C.)
  4. customCrystallization
  5. customthe solid was collected
  6. washwashed with ether
  7. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-b9170f21b2dc4cc5acce12e4b8c5de13
Source dataset
uspto-grants-1993_05
Patent number
US05212035

Linked notes

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