Water → HCID 178423499, compound

Participants

Reaction Steps

to a solution of 0.82 g of 2-mercapto-5-methyl benzimidazole (5 mmoles) in 10 ml of dry THF is added 200 mg of sodium hydride suspension (60% suspension in mineral oil) (5 mmoles). The reaction mixture is heated at reflux temperature for ½ hour. The mixture is then cooled to room temperature and 0.71 g of 5-nitrofuraldehyde (5 mmoles) in 5 ml of THF is added dropwise. The reaction mixture is stirred for ½ hour and then poured into 200 ml of water. The mixture is extracted twice with 75 ml of EtOAc. The combined organic extracts are washed with brine, dried over MgSO4 and concentrated. The crude product is purified on silica gel using DCM/MeOH 97/3 as eluent. 1.07 g of 5-(5-Methyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde is isolated as a black glassy solid (yield=83%). Analytical LC/MS method A: ([M+H]+): 259, RT: 3.64 min (gradient 0 to 50% acetonitrile in 7 min).

Provenance & Evidence