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

HRID 856796노트

반응식

HRID 856796 반응식
[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]

참가 물질

7

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 229386165-(chloromethyl)-1-propyl-1H-imidazole hydrochlorideHCID 178526473HCID 178526473, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a0f5230e973b4f2a888785af7b544c4e
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262185B2

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