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

HRID 398822Notes

Reaction equation

HRID 398822 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 18968812(+/-)-3-((2-Amino-2-ethylhexyl)thio)-4-pyridyl phenyl ketoneYield 27.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d849c3654b8d449889216ec5151aa393
Source dataset
uspto-grants-1998_10
Patent number
US05817652

Reaction notes

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