Sodium Hydroxide → N-[2-[(4-Hydroxyphenyl)sulfonyl]ethyl]-2-propanamine hydrochloride

HRID 4213Notes

Reaction equation

HRID 4213 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][CH2:13][NH:14][CH:15]([CH3:17])[CH3:16])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[OH-:18].[Na+]>CS(C)=O>[ClH:2].[OH:18][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][CH2:13][NH:14][CH:15]([CH3:17])[CH3:16])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13655033N-[2-(4-chlorophenylsulfonyl)ethyl]-2-propanamine hydrochloride

Product 1

HCID 20152889N-[2-[(4-Hydroxyphenyl)sulfonyl]ethyl]-2-propanamine hydrochloride

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of N-[2-[(4-chlorophenyl)sulfonyl]ethyl]-1-methylethanamine hydrochloride and sodium hydroxide in 500 ml of dimethyl sulfoxide is heated at 95° C. for 2 hrs with stirring. The solvent is removed by rotary evaporation (vacuum pump) and the residue is partitioned between water (pH adjusted to 7 by the addition of dilute hydrochloric acid) and chloroform. The chloroform is removed and the residue is converted to the hydrochloride salt with ethereal hydrogen chloride. The salt is then recrystallized from methanol-diethyl ether to give crystalline title compound.

Workup

  1. customThe solvent is removed by rotary evaporation (vacuum pump)
  2. customthe residue is partitioned between water (
  3. additionpH adjusted to 7 by the addition of dilute hydrochloric acid) and chloroform
  4. customThe chloroform is removed
  5. customThe salt is then recrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-53878bc16b5f4166be999b2b304deda7
Source dataset
uspto-grants-1988_02
Patent number
US04724235

Reaction notes

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