1-(1,1'-Biphenyl)-4-yl-2-bromoethanone → HCID 85717302, 화합물

HRID 369839노트

반응식

HRID 369839 반응식
Cl.[CH2:2]([O:4][C:5](=[O:10])[CH2:6][C:7](=[NH:9])[NH2:8])[CH3:3].C([O-])C.[Na+].Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)=O>C(O)C>[NH2:9][C:7]1[NH:8][C:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)=[CH:16][C:6]=1[C:5]([O:4][CH2:2][CH3:3])=[O:10]

참가 물질

5

반응물 3

HCID 672821-(1,1'-Biphenyl)-4-yl-2-bromoethanoneHCID 2723922Sodium ethoxideHCID 15555354Ethyl 2-carbamimidoylacetate hydrochloride

생성물 1

HCID 85717302HCID 85717302, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Under an argon atmosphere, 1.65 g (1 0 mmol) of 2-amidino-acetic acid ethyl ester hydrochloride (for preparation see: Liebigs Ann. Chem., 1895 (1977)) are introduced into 10 ml of ethanol and, at 0-5° C., 0.73 g (10 mmol) of sodium ethanolate is added thereto. The bright yellow suspension is stirred for 20 min and then 1.4 g (5 mmol) of 2-bromo-1-(biphen-4-yl)-ethan-1-one (2-bromo-4'-phenyl-acetophenone; Aldrich; Milwaukee/USA) are added thereto. After 48 hours' stirring at RT, the reaction mixture is concentrated by evaporation and the residue is taken up in ethyl acetate and washed with 3 portions of water and brine. The aqueous phases are extracted twice with ethyl acetate and the organic phases are dried over MgSO4 and concentrated by evaporation. Column chromatography (SiO2 ; ethyl acetate/hexane [1:1]) and stirring in diisopropyl ether/hexane yield the title compound; m.p. 186-188° C.; TLC-Rf =0.17 (ethyl acetate/hexane [1:1]); FAB-MS: (M+H)+ =306.

후처리

  1. stirringAfter 48 hours' stirring at RT
  2. concentrationthe reaction mixture is concentrated by evaporation
  3. washwashed with 3 portions of water and brine
  4. extractionThe aqueous phases are extracted twice with ethyl acetate
  5. dry with materialthe organic phases are dried over MgSO4
  6. concentrationconcentrated by evaporation
  7. stirringColumn chromatography (SiO2 ; ethyl acetate/hexane [1:1]) and stirring in diisopropyl ether/hexane

출처 및 근거

ORD 기록
ord-0a606e52446b483883a4854aa5d94f4e
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06140332

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