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

HRID 888383노트

반응식

HRID 888383 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 61181Mercurous acetate촉매

반응 조건

온도
40 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9baf22b7b0d84bc5876adbbcc9991bde
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247401B2

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