Sodium Hydroxide → N-[2-[(4-Chlorophenyl)sulfinyl]ethyl]-1-methylethanamine

HRID 4188

Reaktionsgleichung

Reaktionsgleichung von HRID 4188
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][NH:11][CH:12]([CH3:14])[CH3:13])=[CH:4][CH:3]=1.B(O[O-])=[O:16].[Na+].[OH-].[Na+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH2:9][CH2:10][NH:11][CH:12]([CH3:14])[CH3:13])=[O:16])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 517072Sodium PerborateHCID 13655026N-[2-[(4-chlorophenyl)thio]ethyl]-1-methylethanamine

Produkt 1

HCID 13655030N-[2-[(4-Chlorophenyl)sulfinyl]ethyl]-1-methylethanamineAusbeute 90,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

A solution of 15.05 g (0.066 mole) of N-[2-[(4-chlorophenyl)thio]ethyl]-1-methylethanamine and 12.0 g (0.0779 mole) of sodium perborate in 400 ml of 1M sulfuric acid was stirred at room temperature for about 18 hr. The solution was made basic with 50% sodium hydroxide and the basic solution was extracted with methylene chloride. The methylene chloride layer was dried with magnesium sulfate and the solvent removed in vacuo to give 14.7 g of solid. Nuclear magnetic resonance analysis showed a 9 to 1 ratio of sulfoxide to sulfide. The solid was recrystallized from ether-hexane to give 12.3 g (76.4%) of the free base title compound as crystalline solid, m.p. 52.5°-53.5° C.

Aufarbeitung

  1. extractionthe basic solution was extracted with methylene chloride
  2. dry with materialThe methylene chloride layer was dried with magnesium sulfate
  3. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1fcdce9b06cf4aeaa6aaa374d1411429
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04724235

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