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

HRID 398822노트

반응식

HRID 398822 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d849c3654b8d449889216ec5151aa393
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05817652

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