ChemicalBook CAS DataBase List 2-CHLORO-1H-BENZIMIDAZOLE-5-CARBOXYLIC ACID

2-CHLORO-1H-BENZIMIDAZOLE-5-CARBOXYLIC ACID synthesis

5synthesis methods

Product Name:2-CHLORO-1H-BENZIMIDAZOLE-5-CARBOXYLIC ACID
CAS Number:933710-78-2
Molecular formula:C8H5ClN2O2
Molecular Weight:196.59

23814-14-4 Synthesis

2-OXO-2,3-DIHYDRO-1H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID

23814-14-4
70 suppliers
$119.00/250mg

2-CHLORO-1H-BENZIMIDAZOLE-5-CARBOXYLIC ACID

933710-78-2
18 suppliers
$499.55/5MG

Yield:933710-78-2 40%

Reaction Conditions:

with trichlorophosphate at 90; for 13 h;

Steps:

5-Carboxy-2-chlorobenzimidazole (11)

A solution of 10 (2.50 g, 14.0 mmol) in POCl3 (20 mL, 215 mmol) was stirred at 90 °C for 13 h. Thereaction was then quenched by addition of water and saturated aq. NaHCO3 at 0 °C. The resultingsuspension was filtered. The residue was washed with AcOEt and purified by silica gel columnchromatography (CHCl3/MeOH = 4/1) to afford 11 (1.11 g, 40%) as a white solid.1H-NMR (500 MHz, DMSO-d6) ? 8.07 (s, 1H), 7.84 (d, J = 8.6 Hz, 1H), 7.57 (d, J = 8.6 Hz, 1H). TheNH and CO2H proton signals were not observed.; ESI-TOF-HRMS calcd for C8H4ClN2O2 (m/z) [M-H]-194.9956, found 194.9965.

References:

Okazaki, Shogo;Sakai, Taki;Ishikawa, Minoru;Hashimoto, Yuichi;Yamaguchi, Takao [Heterocycles,2017,vol. 95,# 1,p. 595 - 607]