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ChemicalBook CAS DataBase List 1H-Benzimidazole,2-pyrazinyl-(9CI)
2602-88-2

1H-Benzimidazole,2-pyrazinyl-(9CI) synthesis

6synthesis methods
-

Yield:2602-88-2 86%

Reaction Conditions:

with tert.-butylhydroperoxide;iodine;zinc(II) iodide in water;acetonitrile at 20; for 3 h;

Steps:

General Procedure for the Synthesis of Benzimadazoles (3a-3i) from 2-aminobenzamides and benzonitriles

General procedure: To an oven dried rb flask with a magnetic stir bar were added 2-amiobenzamide 1a (136.0 mg, 1.0 mmol), nitrile derivative 2 (108.0 mg, 1.0 mmol), anhydrous zinc iodide (0.3 equiv, 96 mg) and the mixture were stirred in 5 mL acetonitrile for 1h at room temperature. Then iodine (51 mg, 0.2 mmol) and aq. TBHP (70% solution in water, 0.26 mL, 2.0 mmol) were added successively and the mixture stirred at rt for another 2 h. After completion of the reaction (TLC monitoring), the reaction mixture was quenched by aq. Na2S2O3 solution (5%, 20 mL), extracted with ethyl acetate (10 mL × 3), and the combined organic part was dried over anhydrous sodium sulphate. Removal of the solvent under reduced pressure left a crude mass which was purified by column chromatography using silica gel (25% EtOAc/hexane) to afford 3a (155 mg; 80% yield).

References:

Saha, Moumita;Das, Asish R. [Tetrahedron Letters,2018,vol. 59,# 26,p. 2520 - 2525] Location in patent:supporting information