Acetonitrile → HCID 86701153、化合物

HRID 1396659ノート

反応式

HRID 1396659 の反応式
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]

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 58575197HCID 58575197、化合物HCID 585754182-(tetrahydrofuran-3-yl)-1H-imidazole

生成物 1

HCID 86701153HCID 86701153、化合物収率 74.6%

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9255f6c0b1494c678cb0fbdeabce02ea
出典データセット
uspto-grants-2014_12
特許番号
US08901126B2

反応ノート

読み込み中…