3'-Aminoacetophenone → N-(3-Acetyl-phenyl)-2-dimethylamino-acetamide

HRID 30610

反応式

HRID 30610 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH2:11]([N:13]([CH2:16]C)[CH2:14]C)[CH3:12].C1C[O:21]CC1>C(O)C>[C:8]([C:4]1[CH:3]=[C:2]([NH:1][C:12](=[O:21])[CH2:11][N:13]([CH3:16])[CH3:14])[CH:7]=[CH:6][CH:5]=1)(=[O:10])[CH3:9]

参加物

5

反応物 3

HCID 74173'-AminoacetophenoneHCID 8028TetrahydrofuranHCID 8471Triethylamine

生成物 1

HCID 22200562N-(3-Acetyl-phenyl)-2-dimethylamino-acetamide収率 85%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 3′-amino-acetophenone (25 mmol) in THF (100 mL) was added chloroacyl chloride (30 mmol). The mixture was stirred for 30 min, poured into ice cold 2M NaOH (aq) and extracted with Et2O. The organic phase was dried and the solvent was removed under reduced pressure giving the pure product. A solution of the product (10 mmol) and triethyl amine (30 mmol) in ethanol was added amine (20 mmol) and the mixture was refluxed for 4 hours. Ethanol was removed under reduced pressure and the product was dissolved in EtOAc and washed with 2M NaOH (aq). EtOAc was removed under reduced pressure giving the product as pure brown oil in 85% yield. 1H-NMR (CDCl3) 5 9.31 (s, 1H), 8.05 (m, 2H), 7.72 (dt,1H), 7.46 (t, 1H), 3.11 (s, 2H), 2.62 (s, 3H), 2.41 (s,.6H).

後処理

  1. extractionextracted with Et2O
  2. customThe organic phase was dried
  3. customthe solvent was removed under reduced pressure
  4. customgiving the pure product
  5. temperaturethe mixture was refluxed for 4 hours
  6. customEthanol was removed under reduced pressure
  7. dissolutionthe product was dissolved in EtOAc
  8. washwashed with 2M NaOH (aq)
  9. customEtOAc was removed under reduced pressure

出典と根拠

ORDレコード
ord-89d5d4a0ec5540d1b85f2c8cfe93de03
出典データセット
uspto-grants-2008_09
特許番号
US07423181B2

関連ノート

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