2-Butyl-2-ethylaziridine → (+/-)-3-((2-Amino-2-ethylhexyl)thio)-4-pyridyl phenyl ketone

HRID 398822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 398822
[C:1]1([C:7]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2Cl)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]([C:20]1([CH2:23][CH3:24])[CH2:22][NH:21]1)[CH2:17][CH2:18][CH3:19].O.[SH2:26].[Na]>CS(C)=O.C(OCC)C>[C:1]1([C:7]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[S:26][CH2:22][C:20]([NH2:21])([CH2:23][CH3:24])[CH2:16][CH2:17][CH2:18][CH3:19])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 217099702-Butyl-2-ethylaziridineHCID 53442613Sodium hydrogen sulfide hydrateHCID 53761854(3-Chloropyridin-4-yl)(phenyl)methanone

Produkt 1

HCID 18968812(+/-)-3-((2-Amino-2-ethylhexyl)thio)-4-pyridyl phenyl ketoneAusbeute 27,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of the product from step (b) (4.3 g), 2-butyl-2-ethylaziridine (2.54 g, Synthetic Example 1(f)), and sodium hydrogen sulfide hydrate (1.48 g) in dimethylsulfoxide was stirred 48 hours at ambient temperature. The reaction mixture was diluted with diethyl ether and washed with aqueous sodium hydroxide, dried, filtered and evaporated to a yellow viscous oil. The oil was chromatographed on silica gel using ethyl acetate-ethanol (3:1) as eluant to give a yellow viscous oil (1.87 g). 1H NMR is consistent with proposed structure.

Aufarbeitung

  1. washwashed with aqueous sodium hydroxide
  2. customdried
  3. filtrationfiltered
  4. customevaporated to a yellow viscous oil
  5. customThe oil was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-d849c3654b8d449889216ec5151aa393
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05817652

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