Water → 5-Nitro-2-(((1-propylimidazol-5-yl)methyl)sulfanyl)benzimidazole

HRID 856796ノート

反応式

HRID 856796 の反応式
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.C(N(CC)CC)C.Cl.Cl[CH2:23][C:24]1[N:28]([CH2:29][CH2:30][CH3:31])[CH:27]=[N:26][CH:25]=1.O>O1CCCC1.CO>[N+:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([S:1][CH2:23][C:24]3[N:28]([CH2:29][CH2:30][CH3:31])[CH:27]=[N:26][CH:25]=3)[NH:3][C:4]=2[CH:10]=1)([O-:13])=[O:12]

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 229386165-(chloromethyl)-1-propyl-1H-imidazole hydrochlorideHCID 178526473HCID 178526473、化合物

生成物 1

HCID 229387045-Nitro-2-(((1-propylimidazol-5-yl)methyl)sulfanyl)benzimidazole収率 68.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-mercapto-5-nitrobenzimidazole (3.0 g) and triethylamine (12.5 ml) in tetrahydrofuran (30 ml) was added dropwise a solution of 5-chloromethyl-1-propylimidazole hydrochloride (3.0 g) in methanol (30 ml) under nitrogen atmosphere at 0° C. After the mixture was allowed to be at room temperature and stirred for 10 minutes, water was added to the mixture and the mixture was extracted with ethyl acetate twice. The mixture was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (methanol:ethyl acetate=1:8→methanol:ethyl acetate=1:4), which was recrystallized from diisopropyl ether-ethyl acetate, to give 5-nitro-2-(((1-propylimidazol-5-yl)methyl)sulfanyl)benzimidazole (3.33 g) as yellow crystals.

後処理

  1. customto be at room temperature
  2. extractionthe mixture was extracted with ethyl acetate twice
  3. dry with materialThe mixture was dried over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (methanol:ethyl acetate=1:8→methanol:ethyl acetate=1:4), which
  6. customwas recrystallized from diisopropyl ether-ethyl acetate

出典と根拠

ORDレコード
ord-a0f5230e973b4f2a888785af7b544c4e
出典データセット
uspto-grants-2007_08
特許番号
US07262185B2

反応ノート

読み込み中…