4-Toluenesulfonyl chloride → HCID 67600028, compound

HRID 1417311Notes

Reaction equation

HRID 1417311 reaction equation
Cl.[N+:2]([C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])=[CH:7][CH:6]=1)([O-:4])=[O:3].[OH-].[Na+].[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>O.C(OCC)C>[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:14][CH2:13][CH2:12][CH2:11][CH2:10][O:9][C:8]2[CH:15]=[CH:16][C:5]([N+:2]([O-:4])=[O:3])=[CH:6][CH:7]=2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 67600070HCID 67600070, compound

Product 1

HCID 67600028HCID 67600028, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 8.8 g of 4-(4-nitrophenoxy)-butaneamine hydrochloride (Example 34) in 200 ml of water is treated successively with 9 ml of 10N NaOH, and a solution of 7.5 g of 4-methylbenzenesulfonyl chloride in 200 ml of diethylether. The reaction is stirred at room temperature for 3 hours, the precipitate collected, washed with water and diethylether, and air dried. Recrystallization from 50% aqueous ethanol gives the desired product as a solid, m.p. 87°-88° C.; yield, 1.2 g.

Workup

  1. customthe precipitate collected
  2. washwashed with water and diethylether, and air
  3. customdried
  4. customRecrystallization from 50% aqueous ethanol

Sources & evidence

ORD record
ord-b212ad2ba8e04f82aaae4bce559fd0c1
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

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