Sodium Iodide → HCID 66987547, Verbindung

HRID 555274Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 555274
[CH3:1][O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[N:9]([CH2:12][CH2:13][OH:14])[CH:10]=[N:11][C:7]=2[CH:6]=1)=[O:4].[H-].[Na+].[CH3:19][S:20][CH2:21]Cl.[Na+].[I-]>CCCC[N+](CCCC)(CCCC)CCCC.[I-].COCCOC.C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[N:9]([CH2:12][CH2:13][O:14][CH2:19][S:20][CH3:21])[CH:10]=[N:11][C:7]=2[CH:6]=1)=[O:4]

Komponenten

8

Edukt 4

HCID 5238Sodium IodideHCID 16916Chloromethyl methyl sulfideHCID 24758Sodium hydrideHCID 66987301HCID 66987301, Verbindung

Produkt 1

HCID 66987547HCID 66987547, VerbindungAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A solution of 1-(2-hydroxyethyl)-1H-benzimidazole-5-carboxylic acid methyl ester (0.5 g. 2.27 mmol) in a mixture of dry THF:DME (25 mL:15 mL) was cooled to 5° C. NaH (0.081 g, 3.4 mmol) was added and stirred for 30 min at the same temperature. A mixture of chloromethyl methyl sulphide (0.285 g, 2.95 mmol) and NaI (0.408 g, 2.95 mmol) was then added slowly followed by TBAI (0.087 g, 0.22 mmol). The reaction was allowed to stir for overnight at ambient temperature. It was then quenched with saturated ammonium chloride solution and extracted with EtOAc. The organic layer was evaporated to give 0.53 g (83%) of 1-(2-methylsulfanylmethoxyethyl)-1H-benzimidazole-5-carboxylic acid methyl ester. 1H NMR (300 MHz, CDCl3) δ 1.9 (s, 3H), 3.9 (t, 2H), 3.95 (s, 3H), 4.4 (t, 2H), 4.6 (s, 2H), 7.45 (d, 1H), 8.05 (m, 2H), 8.5 (d, 1H)

Aufarbeitung

  1. additionwas then added slowly
  2. stirringto stir for overnight at ambient temperature
  3. customIt was then quenched with saturated ammonium chloride solution
  4. extractionextracted with EtOAc
  5. customThe organic layer was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-c77c16136906438694f71f21c8229dd7
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053431B2

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