2,5-Difluorobenzonitrile → 5-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile

HRID 348144

反応式

HRID 348144 の反応式
F[C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[C:4]#[N:5].[Na].[NH:12]1[CH:16]=[N:15][CH:14]=[N:13]1>CN(C)C=O.C(Cl)Cl>[F:10][C:7]1[CH:8]=[CH:9][C:2]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[C:3]([CH:6]=1)[C:4]#[N:5]

参加物

5

反応物 2

HCID 1235582,5-DifluorobenzonitrileHCID 454898221h-1,2,4-Triazole sodium salt

生成物 1

HCID 218662545-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile収率 49%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

A suspension of 2,5-diflurobenzonitrile (4.5 g, 32.35 mmol) and 1,2,4-triazole sodium salt (3.6 g, 40 mmol) in dimethylformamide (40 mL) was heated at 80° C. for 15 h. The reaction mixture was then cooled, diluted with CH2Cl2 (200 mL), washed with water (3×30 mL) and brine (30 mL), then dried (Na2SO4), filtered and concentrated to give a white solid which was purified by flash column chromatography (SiO2) using 1:1 to 3:1 ethyl acetate/Hexanes to afford the title compound (2.98 g, 49% yield) as a white powder. 1H NMR (500 MHz, CDCl3) δ: 8.70 (1H, s), 8.18 (1H, s), 7.76 (1H, dd, J=9.0, 4.8 Hz), 7.55 (1H, dd, J=7.3, 2.8 Hz), 7.51–7.47 (1H, m). LCMS (M+H) calcd for C9H6FN4: 189.17; found: 189.10.

後処理

  1. temperatureThe reaction mixture was then cooled
  2. washwashed with water (3×30 mL) and brine (30 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a white solid which
  7. customwas purified by flash column chromatography (SiO2)

出典と根拠

ORDレコード
ord-d325230ac27e464fa2901268306b27ca
出典データセット
uspto-grants-2007_02
特許番号
US07176196B2

関連ノート

読み込み中…