Dimethylformamide → 3-(4-bromophenyl)-N-methylpropanamide

HRID 746761노트

반응식

HRID 746761 반응식
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([OH:18])=O)=[CH:10][CH:9]=1.[CH3:19][N:20](C=O)C.CN>C(Cl)Cl.C1COCC1.O>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([NH:20][CH3:19])=[O:18])=[CH:10][CH:9]=1

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 6329MethylamineHCID 65578Oxalyl chlorideHCID 27356093-(4-Bromophenyl)propionic acid

생성물 1

HCID 178950553-(4-bromophenyl)-N-methylpropanamide수율 41%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Add oxalyl chloride (1.75 mL, 2.54 g, 4 eq.) to a solution of 3-(4-bromo-phenyl)-propionic acid in methylene chloride (100 mL), which contains 0.1 mL DMF at 0° C. and allow the reaction mixture to warm to room temperature and stir 1 hour. Evaporate solvent and dissolve it in 10 mL THF. Add half of the THF solution to 20 mL of methylamine (2M) and stir another hour. Add water to the solution to dissolve solid and wash organic layer with 2N HCl, water and saturated aq. sodium chloride and dry it over MgSO4. Evaporate solvent to afford the title compound 500 mg, 41%. MS 246.0.

후처리

  1. customat 0° C.
  2. stirringstir another hour
  3. washwash organic layer with 2N HCl, water and saturated aq. sodium chloride
  4. dry with materialdry it over MgSO4

출처 및 근거

ORD 기록
ord-4e22665ef614418b869b1e3e5ea97d0d
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07393868B2

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