Acetonitrile → HCID 86701153, 화합물

HRID 1396659노트

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HRID 1396659 반응식
F[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:15][O:16][CH3:17])[CH:3]=1.[O:18]1[CH2:22][CH2:21][CH:20]([C:23]2[NH:24][CH:25]=[CH:26][N:27]=2)[CH2:19]1.C(#N)C>C(N(CC)CC)C>[CH3:17][O:16][CH2:15][C:4]1[CH:3]=[C:2]([N:24]2[CH:25]=[CH:26][N:27]=[C:23]2[CH:20]2[CH2:21][CH2:22][O:18][CH2:19]2)[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 58575197HCID 58575197, 화합물HCID 585754182-(tetrahydrofuran-3-yl)-1H-imidazole

생성물 1

HCID 86701153HCID 86701153, 화합물수율 74.6%

시약·촉매·용매 1

HCID 8471Triethylamine용매

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온도
70 °C

실험 절차

To a mixture of 6.0 g of methyl 4-fluoro-2-(methoxymethyl)-5-nitrobenzoate, 3.5 g of 2-(tetrahydrofuran-3-yl)-1H-imidazole, and 60 mL of acetonitrile was added 6.9 mL of triethylamine, followed by stirring at 70° C. for 5.5 hours. The reaction mixture was concentrated, and water and ethyl acetate were added thereto, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 6.65 g of methyl 2-(methoxymethyl)-5-nitro-4-[2-(tetrahydrofuran-3-yl)-1H-imidazol-1-yl]benzoate.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additionwater and ethyl acetate were added
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

출처 및 근거

ORD 기록
ord-9255f6c0b1494c678cb0fbdeabce02ea
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901126B2

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