Tetrahydrofuran → Methyl 3-(5-methylpyridin-2-yl)-5-(4-methyl-4H-1,2,4-triazol-3-yl)benzoate

HRID 888383ノート

反応式

HRID 888383 の反応式
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=2)[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])=S.C([NH:24][NH2:25])=O.[CH2:26]1COCC1>C([O-])(=O)C.[Hg+]>[CH3:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[CH:12]=[C:7]([CH:6]=[C:5]([C:3]3[N:2]([CH3:26])[CH:1]=[N:25][N:24]=3)[CH:14]=2)[C:8]([O:10][CH3:11])=[O:9])=[N:16][CH:17]=1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 12229HydrazinecarboxaldehydeHCID 86646758Methyl 3-[(methylamino)carbonothioyl]-5-(5-methylpyridin-2-yl)benzoate

生成物 1

HCID 68498660Methyl 3-(5-methylpyridin-2-yl)-5-(4-methyl-4H-1,2,4-triazol-3-yl)benzoate

試薬・触媒・溶媒 1

HCID 61181Mercurous acetate触媒

反応条件

温度
40 °C

実験手順

To a solution of methyl 3-[(methylamino)carbonothioyl]-5-(5-methylpyridin-2-yl)benzoate (0.90 g, 3.00 mmol) in THF (30 mL) was added formic hydrazide (0.54 g, 8.99 mmol) and mercury acetate (1.72 g, 5.39 mmol) and the mixture heated to 40° C. After 16 h, the reaction was cooled to ambient temperature, filtered and concentrated. The organic residue was dissolved in 100 ml of dichloromethane and washed with 50 mL of saturated aqueous sodium bicarbonate (2×). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (100% dichloromethane→90% dichloromethane/methanol) to give the title compound (0.37 g). MS 309.1 (M+1).

後処理

  1. temperaturethe reaction was cooled to ambient temperature
  2. filtrationfiltered
  3. concentrationconcentrated
  4. dissolutionThe organic residue was dissolved in 100 ml of dichloromethane
  5. washwashed with 50 mL of saturated aqueous sodium bicarbonate (2×)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography (100% dichloromethane→90% dichloromethane/methanol)

出典と根拠

ORDレコード
ord-9baf22b7b0d84bc5876adbbcc9991bde
出典データセット
uspto-grants-2012_08
特許番号
US08247401B2

反応ノート

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