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

HRID 253476
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 253476
[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]
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Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6e5000b5af3948089cfc1951e1941618
Quelldatensatz
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07872018B2

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