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1-Chloromethylnaphthalene → 2-((5,6-Dimethyl-1-(1-naphthylmethyl)benzimidazole-2-ylthio)methyl)benzoic acid methyl ester

HRID 916078
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HRID 916078 반응식
[H-].[Na+].O1CCCC1.[CH3:8][O:9][C:10](=[O:30])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][S:18][C:19]1[NH:20][C:21]2[CH:27]=[C:26]([CH3:28])[C:25]([CH3:29])=[CH:24][C:22]=2[N:23]=1.Cl[CH2:32][C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][CH:34]=1>O>[CH3:8][O:9][C:10](=[O:30])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][S:18][C:19]1[N:20]([CH2:32][C:33]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:36]=[CH:35][CH:34]=2)[C:21]2[CH:27]=[C:26]([CH3:28])[C:25]([CH3:29])=[CH:24][C:22]=2[N:23]=1
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참가 물질

6

반응물 4

HCID 68451-ChloromethylnaphthaleneHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 154876332-((5,6-Dimethylbenzimidazole-2-ylthio)methyl)benzoic acid methyl ester

생성물 1

HCID 694584962-((5,6-Dimethyl-1-(1-naphthylmethyl)benzimidazole-2-ylthio)methyl)benzoic acid methyl ester수율 32%

시약·촉매·용매 1

HCID 962
Water
용매

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온도
60 °C

실험 절차

Sodium hydride (1.1 mg, 0.306 mmol) and 2 ml of tetrahydrofuran was added to a previously dried reaction vessel. To the mixture were added 2-((5,6-dimethylbenzimidazole-2-ylthio)methyl)benzoic acid methyl ester (50 mg, 0.153 mmol) and 1-chloromethylnaphthalene (69 μl, 0.459 mmol), which was then stirred at 60° C. for 45 minutes. Water was added thereto, followed by extraction with ethyl acetate. After drying the ethyl acetate phase with anhydrous sodium sulfate, it was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 2-((5,6-dimethyl-1-(1-naphthylmethyl)benzimidazole-2-ylthio)methyl)benzoic acid methyl ester (yield 32%).

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialAfter drying the ethyl acetate phase with anhydrous sodium sulfate, it
  3. concentrationwas concentrated
  4. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-d366722509e94ac6b6606aaa7976705b
출처 데이터셋
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07268145B2

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