Dimethylformamide → 4-(1H-benzoimidazol-2-ylmethoxy)-2-chloro-5-methoxy-benzaldehyde

HRID 253455

反応式

HRID 253455 の反応式
[Cl: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].CN(C)C=O.[H-].[Na+].[NH:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[C:21]1[CH2:29]OC1C(Cl)=CC(C=O)=C(F)C=1>>[NH:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[C:21]1[CH2:29][O:10][C:8]1[C:7]([O:11][CH3:12])=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([Cl:1])[CH:9]=1

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 290002-Chloro-4-hydroxy-5-methoxybenzaldehydeHCID 598038544-(1H-benzoimidazol-2-ylmethoxy)-5-chloro-2-fluoro-benzaldehyde

生成物 1

HCID 598038904-(1H-benzoimidazol-2-ylmethoxy)-2-chloro-5-methoxy-benzaldehyde

反応条件

温度
80 °C

実験手順

2-Chloro-4-hydroxy-5-methoxy-benzaldehyde (136, 2.30 g, 0.0123 mol) was dissolved in N,N-dimethylformamide (89.5 mL, 1.16 mol) and sodium hydride (60% dispersion in mineral oil, 541 mg, 0.0135 mol) was added. After 20 minutes, 2-chloromethyl-1H-benzoimidazole (106, 2.05 g, 0.0123 mol) was added to the reaction. The reaction was stirred at 80° C. overnight. The reaction was concentrated in vacuo to an oil. Ethyl acetate was added and washed with saturated sodium bicarbonate and brine. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 30-70% ethyl acetate in hexane over 30 minutes to provide a white solid (137, 1.79 g, 46%). MS (ESI) [M+H+]+=317.1, 319.1.

後処理

  1. concentrationThe reaction was concentrated in vacuo to an oil
  2. additionEthyl acetate was added
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography
  8. washeluting with 30-70% ethyl acetate in hexane over 30 minutes
  9. customto provide a white solid (137, 1.79 g, 46%)

出典と根拠

ORDレコード
ord-fc39b84c238541d1868b16b5ef595e9e
出典データセット
uspto-grants-2011_01
特許番号
US07872018B2

関連ノート

読み込み中…