Potassium Carbonate → 2-[2-(3-bromo-phenyl)-2-hydroxy-ethylamino]-N-phenyl-acetamide

HRID 560116

反応式

HRID 560116 の反応式
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=1)[OH:4].Cl[CH2:13][C:14]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:15].C(=O)([O-])[O-].[K+].[K+].OP([O-])(O)=O.[K+]>C(#N)C.C(OCC)(=O)C>[Br:11][C:7]1[CH:6]=[C:5]([CH:3]([OH:4])[CH2:2][NH:1][CH2:13][C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:15])[CH:10]=[CH:9][CH:8]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 11485ChloroacetanilideHCID 516951Monobasic potassium phosphateHCID 220210672-Amino-1-(3-bromophenyl)ethan-1-ol

生成物 1

HCID 670006572-[2-(3-bromo-phenyl)-2-hydroxy-ethylamino]-N-phenyl-acetamide収率 42.3%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2-amino-1-(3-bromo-phenyl)-ethanol (example 33, step 1, 1.34 g) and crude 2-chloro-N-phenyl-acetamide (example 33, step 2, 1.0 g) in acetonitrile (15 mL) was added potassium carbonate (1.03 g). The mixture was heated to 80° C. overnight. A 1M solution of KH2PO4 was added, followed by ethyl acetate. The phases were separated, and the inorganic one was extracted with ethyl acetate (x2). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo. Column chromatography (SiO2, CH2Cl2/MeOH 95:5) followed by precipitation from a mixture of diethylether/n-heptane (1:4) gave 2-[2-(3-bromo-phenyl)-2-hydroxy-ethylamino]-N-phenyl-acetamide (0.87 g, 42%) as a white solid, MS: 349.1 (M+H, 1Br)+.

後処理

  1. customThe phases were separated
  2. extractionthe inorganic one was extracted with ethyl acetate (x2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customColumn chromatography (SiO2, CH2Cl2/MeOH 95:5) followed by precipitation from a mixture of diethylether/n-heptane (1:4)

出典と根拠

ORDレコード
ord-e54f51f2b32547079b951d7506d0e604
出典データセット
uspto-grants-2011_11
特許番号
US08063088B2

関連ノート

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