Methyl iodide → 1,5-Dimethyl-4-nitro-1H-pyrazole

HRID 1478080노트

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HRID 1478080 반응식
[CH3:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][NH:4][N:3]=1.CI.[C:12]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:12][N:3]1[C:2]([CH3:1])=[C:6]([N+:7]([O-:9])=[O:8])[CH:5]=[N:4]1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178434564HCID 178434564, 화합물

생성물 1

HCID 5446471,5-Dimethyl-4-nitro-1H-pyrazole수율 22.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

To a solution of 3-methyl-4-nitro-1H-pyrazole (4.01 g, 31.6 mmol) in DMF (60 mL) were added CH3I (8.93 g, 63.0 mmol) and K2CO3 (8.73 g, 63.2 mmol). The reaction mixture was stirred at 60° C. in a sealed tube overnight and concentrated in vacuo. The residue was diluted with water (50 mL), and extracted with EtOAc (50 mL×3). The combined organic phases were washed with brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/2) to give the title compound as a beige solid (1.01 g, 22.7%).

후처리

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with water (50 mL)
  3. extractionextracted with EtOAc (50 mL×3)
  4. washThe combined organic phases were washed with brine (50 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/2)

출처 및 근거

ORD 기록
ord-fbdc1fc1d75a40f989be6c945d066829
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403801B2

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