Glycolic Acid → HCID 67975586, compound

Participants

Reaction Conditions

Reaction Steps

Glycolic acid (1.98 g, 26 mmol, 3 eq.) was added to a solution of 4-chloro-N1-[3-(1H-imidazol-1-yl)propyl]benzene-1,2-diamine (12, 2.18 g, 8.7 mmol) in HCl (6N, 20 mL) at room temperature. The reaction mixture was heated up until 90° C. during 16 hours. After cooling to ambient temperature the reaction mixture was diluted with 100 mL water followed by addition of NaHCO3 until the pH was approximately 7. CH2Cl2 (30 ml) was added and the organic layer was separated and the aqueous layer was further extracted with additional CH2Cl2 (20 mL). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo and purified by flash chromatography (0 to 10% MeOH in CH2Cl2) to give {5-chloro-1-[3-(1H-imidazol-1-yl)propyl]-1H-benzimidazol-2-yl}methanol (13, 740 mg, 30%) as a white solid; LCMS m/z=291 (M+H)+

Provenance & Evidence