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

HRID 746761ノート

反応式

HRID 746761 の反応式
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

参加物

8

反応物 4

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

生成物 1

HCID 178950553-(4-bromophenyl)-N-methylpropanamide収率 41%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4e22665ef614418b869b1e3e5ea97d0d
出典データセット
uspto-grants-2008_07
特許番号
US07393868B2

反応ノート

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