1-Bromo-2-Chloroethane → 3'-[(2-Bromoethyl)oxy]-4-biphenylcarboxamide

HRID 70256노트

반응식

HRID 70256 반응식
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH2:16])=[O:15])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Br:17][CH2:18][CH2:19][Cl:20].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O.C(OCC)(=O)C>[Cl:20][CH2:19][CH2:18][O:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH2:16])=[O:15])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Br:17][CH2:18][CH2:19][O:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH2:16])=[O:15])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 582763863'-Hydroxy-[1,1'-biphenyl]-4-carboxamide

생성물 2

HCID 582762623'-[(2-Bromoethyl)oxy]-4-biphenylcarboxamideHCID 582763523'-[(2-Chloroethyl)oxy]-4-biphenylcarboxamide

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매2회HCID 8857Ethyl Acetate용매

실험 절차

Into three separate microwave vials was distributed equally a mixture of 3′-hydroxy-4-biphenylcarboxamide (Intermediate A-1-1) (1.0 g, 0.005 mol), 1-bromo-2-chloroethane (2.8 g, 0.02 mol) and potassium carbonate (2.8 g, 0.02 mol) in ethanol (2.2 mL) and water (1.8 mL) was placed in a microwave at 150° C. until the reaction was complete as determined by LC/MS. The contents of the vials were combined and diluted with ethyl acetate and water. The aqueous phase was extracted with ethyl acetate. The combined organic phase was dried (Na2SO4), filtered and concentrated in vacuo to give 3′-[(2-chloroethyl)oxy]-4-biphenylcarboxamide and 3′-[(2-bromoethyl)oxy]-4-biphenylcarboxamide as an off-white solid. LC/MS indicates that this product is a mixture of the chloroethoxy (M+H) 276, 2.34 min. (LC/MS method A) and the bromoethoxy (M+H) 320, tR 2.42 min. in a ratio of ˜81/19% respectively. This product was used without further purification.

후처리

  1. customInto three separate microwave vials
  2. customwas placed in a microwave at 150° C. until the reaction
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-78ed0760cfef441a912e458f48109a79
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822518B2

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