Dimethyl Sulfoxide → 3-(1-methyl-1H-benzo[d]imidazol-5-yl)-3-oxopropanenitrile

HRID 1399917

Reaktionsgleichung

Reaktionsgleichung von HRID 1399917
CS(C)=O.[H-].[Na+].[CH3:7][N:8]1[C:12]2[CH:13]=[C:14]([C:17]([O:19]C)=O)[CH:15]=[CH:16][C:11]=2[N:10]=[CH:9]1.[CH3:21][N:22]1[C:26]2[CH:27]=[CH:28][C:29]([C:31]([O:33]C)=O)=[CH:30][C:25]=2[N:24]=[CH:23]1>CC#N>[CH3:7][N:8]1[C:12]2[CH:13]=[C:14]([C:17](=[O:19])[CH2:25][C:26]#[N:22])[CH:15]=[CH:16][C:11]=2[N:10]=[CH:9]1.[CH3:21][N:22]1[C:26]2[CH:27]=[CH:28][C:29]([C:31](=[O:33])[CH2:11][C:12]#[N:8])=[CH:30][C:25]=2[N:24]=[CH:23]1

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 965319Methyl 1-methyl-1H-benzo[d]imidazole-5-carboxylateHCID 10583823Methyl 1-methyl-1H-benzo[d]imidazole-6-carboxylate

Produkt 2

HCID 867293023-(1-methyl-1H-benzo[d]imidazol-6-yl)-3-oxopropanenitrileHCID 867293033-(1-methyl-1H-benzo[d]imidazol-5-yl)-3-oxopropanenitrileAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

A mixture of CH3CN (0.62 mL, 11.84 mmol), DMSO (2 mL) and NaH (410 mg, 10.26 mmol) was stirred for 45 minutes at room temperature before a solution of methyl 1-methyl-1H-benzo[d]imidazole-6-carboxylate and methyl 1-methyl-1H-benzo[d]imidazole-5-carboxylate (1.5 g, 7.89 mmol) in CH3CN (5 mL) was added dropwise. The resulting mixture was stirred at room temperature for 2 h before quenching by the addition of saturated NH4Cl and extraction with DCM (3×30 ml). The combined organic layers were concentrated to give the desired products 3-(1-methyl-1H-benzo[d]imidazol-6-yl)-3-oxopropanenitrile and 3-(1-methyl-1H-benzo[d]imidazol-5-yl)-3-oxopropanenitrile (600 mg, 38%) and used in the next step without further purification. LCMS (m/z): 200.07 (M+1).

Aufarbeitung

  1. additionwas added dropwise
  2. custombefore quenching by the addition of saturated NH4Cl and extraction with DCM (3×30 ml)
  3. concentrationThe combined organic layers were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-061694533e4f4f89912683ed3ee68ff0
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906900B2

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