Reaktion #626405

Reaktionsgleichung

methyl 6-(4-morpholinyl)-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate

N,N-Dimethylaniline

POCl3

→

desired product

Ausbeute 23.0%

methyl 2-chloro-5-(4-morpholinyl)-1H-benzimidazole-7-carboxylate

Ausbeute 23.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was cooled to room temperature
2. 2
   Sonstigepurified by chromatography (eluted with petroleum ether/EtOAc=1/1) on silica

Vorschrift

To a solution of combined batches of methyl 6-(4-morpholinyl)-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate (6.8 g, 24.5 mmol) in POCl3 (25 mL) was added N,N-Dimethylaniline (8.8 g, 73.5 mmol) and the mixture was heated to 103° C. for 12 h. When TLC analysis showed no starting material remaining, the mixture was cooled to room temperature, purified by chromatography (eluted with petroleum ether/EtOAc=1/1) on silica to afford the desired product as a off-white solid (1.6 g, 23%). 1H NMR (300 MHz, DMSO-d6): δ ppm 3.11 (t, 4H, J=4.5 Hz), 3.77 (t, 4H, J=4.5 Hz), 3.93 (s, 3H), 7.43 (d, 1H, J=1.8 Hz), 7.50 (d, 1H, J=1.8 Hz), 12.97 (s, 1H). LC-MS: m/e=296 [M+1]+.

Quelle