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

HRID 916078
ノート
印刷プレビュー

反応式

HRID 916078 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

反応条件

温度
60 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-d366722509e94ac6b6606aaa7976705b
出典データセット
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07268145B2

反応ノート

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