Sodium hydride → 2-(5-fluoro-4-formyl-2-methoxy-phenoxymethyl)-1H-benzoimidazole-5-sulfonic acid dimethylamide

HRID 253476

反応式

HRID 253476 の反応式
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[C:7]([O:11][CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].Cl.[CH3:16][N:17]([CH3:32])[S:18]([C:21]1[CH:31]=[CH:30][C:24]2[NH:25][C:26]([CH2:28]Cl)=[N:27][C:23]=2[CH:22]=1)(=[O:20])=[O:19]>CN(C)C=O>[CH3:32][N:17]([CH3:16])[S:18]([C:21]1[CH:31]=[CH:30][C:24]2[NH:25][C:26]([CH2:28][O:10][C:8]3[CH:9]=[C:2]([F:1])[C:3]([CH:4]=[O:5])=[CH:6][C:7]=3[O:11][CH3:12])=[N:27][C:23]=2[CH:22]=1)(=[O:19])=[O:20]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 5981552-Fluoro-4-hydroxy-5-methoxybenzaldehydeHCID 1784861302-Chloromethyl-1h-benzoimidazole-5-sulfonic acid dimethylamide hydrochloride salt

生成物 1

HCID 1784926252-(5-fluoro-4-formyl-2-methoxy-phenoxymethyl)-1H-benzoimidazole-5-sulfonic acid dimethylamide収率 17%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

2-Fluoro-4-hydroxy-5-methoxy-benzaldehyde (39, 0.38 g, 2.2 mmol) was dissolved in N,N-dimethylformamide (30 mL) and sodium hydride 60% dispersion in mineral oil (120 mg) was added. After 20 minutes, 2-chloromethyl-1H-benzoimidazole-5-sulfonic acid dimethylamide hydrochloride salt (217, 0.559 g, 1.80 mmol) was added to the mixture. The reaction was stirred at 60° C. overnight. The solvent was removed under reduced pressure. Ethyl acetate was added and the organic layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with a gradient of ethyl acetate (20-100%) in hexane to provide the desired compound (218, 0.122 g, 17%).

後処理

  1. customThe solvent was removed under reduced pressure
  2. additionEthyl acetate was added
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography
  8. washeluting with a gradient of ethyl acetate (20-100%) in hexane

出典と根拠

ORDレコード
ord-6e5000b5af3948089cfc1951e1941618
出典データセット
uspto-grants-2011_01
特許番号
US07872018B2

関連ノート

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