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Acetic Anhydride → (E)-N-(4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl)benzyl)acetamide

HRID 587262
ノート
印刷プレビュー

反応式

HRID 587262 の反応式
Cl[C:2]1[CH:7]=[C:6](/[CH:8]=[CH:9]/[CH:10]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[CH:16]=2)[C:11]([F:14])([F:13])[F:12])[CH:5]=[CH:4][C:3]=1[CH2:23][NH2:24].[C:25](OC(=O)C)(=[O:27])[CH3:26]>C(Cl)Cl.O>[Cl:22][C:17]1[CH:16]=[C:15]([CH:10]([C:11]([F:14])([F:12])[F:13])/[CH:9]=[CH:8]/[C:6]2[CH:7]=[CH:2][C:3]([CH2:23][NH:24][C:25](=[O:27])[CH3:26])=[CH:4][CH:5]=2)[CH:20]=[C:19]([Cl:21])[CH:18]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 7918Acetic AnhydrideHCID 86675181(E)-(2-chloro-4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-en-1-yl)phenyl)methanamine

生成物 1

HCID 86675197(E)-N-(4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl)benzyl)acetamide収率 62.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of (E)-(2-chloro-4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-en-1-yl)phenyl)methanamine (0.3 g, 0.8 mmol) in CH2Cl2 (10 mL) was added acetic anhydride (0.12 mL, 1.14 mmol), and TEA (0.217 mL, 1.52 mmol), and the resultant reaction mixture was stirred at ambient temperature for 6 h. The reaction mixture was diluted with water and extracted with CH2Cl2. The combined CH2Cl2 layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Purification by flash column chromatography (SiO2, 100-200 mesh; 30-50% EtOAc in hexane) afforded the title compound as a off-white solid (0.2 g, 60%) mp 107-109° C.; 1H NMR (400 MHz, CDCl3) δ 7.37 (m, 3H), 7.28 (m, 4H), 6.60 (d, J=16.0 Hz, 1H), 6.36 (dd, J=16.0, 8.0 Hz, 1H), 5.75 (br s, 1H), 4.46 (d, J=6 Hz, 2H), 4.01 (m, 1H), 2.11 (s, 3H); ESIMS m/z 402.00 ([M+H]+).

後処理

  1. customthe resultant reaction mixture
  2. extractionextracted with CH2Cl2
  3. washThe combined CH2Cl2 layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash column chromatography (SiO2, 100-200 mesh; 30-50% EtOAc in hexane)

出典と根拠

ORDレコード
ord-fd66db8134fc4891b77bd27c6c0953cb
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09226500B2

反応ノート

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