Sodium Hydroxide → N-[-(Phenylsulfinyl)ethyl]-2-propanamine maleate

HRID 4208

Reaction equation

HRID 4208 reaction equation
Cl.[C:2]1([S:8][CH2:9][CH2:10][NH:11][CH:12]([CH3:14])[CH3:13])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B1([O-])O[O:16]1.[OH2:19].[OH2:20].[OH2:21].[OH2:22].[Na+].[OH-].[Na+]>S(=O)(=O)(O)O>[C:2]([OH:22])(=[O:21])/[CH:3]=[CH:4]\[C:5]([OH:20])=[O:19].[C:2]1([S:8]([CH2:9][CH2:10][NH:11][CH:12]([CH3:14])[CH3:13])=[O:16])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 13655077N-[2-(Phenylthio)ethyl]-2-propanamine hydrochlorideHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

Product 1

HCID 13655081N-[-(Phenylsulfinyl)ethyl]-2-propanamine maleateYield 177.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 15.62 g (0.067 mole) of N-[2-(phenylthio)ethyl]-2-propanamine hydrochloride and 15.62 g (0.101 mole) of sodium perborate tetrahydrate in 300 ml of 2M sulfuric acid was stirred at room temperature for 16 hr. The solution was made basic with 50% sodium hydroxide, and the basic solution was extracted with methylene chloride. The methylene chloride solution was dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was dissolved in ether, a solution of maleic acid in methanol was added, and precipitated to give 19.48 g (88.3%) of white solid, m.p. 102.5°-103.5° C. A sample of this was recrystallized from methanol-ether, m.p. 102.5°-103.5° C.

Workup

  1. extractionthe basic solution was extracted with methylene chloride
  2. dry with materialThe methylene chloride solution was dried over magnesium sulfate
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in ether
  5. additiona solution of maleic acid in methanol was added
  6. customprecipitated

Sources & evidence

ORD record
ord-df95688818af431f92f3b925fa45e917
Source dataset
uspto-grants-1988_02
Patent number
US04724235

Linked notes

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