5-Nitrofurfural → HCID 86623883, compound

Participants

Reaction Steps

Aldehyde intermediate preparation: A mixture of sodium hydride (60% dispersion in mineral oil, 0.338 g, 8.46 mmol) and 2-mercapto-5-chloro-6-methyl-1H-benzimidazole (1.05 g, 5.29 mmol) in 35 ml of tetrahydrofuran is stirred at room temperature for 2 hours. 5-nitro-2-furaldehyde (0.746 g, 5.29 mmol) in 7 ml of tetrahydrofuran is then added dropwise over a 15 minute period and the mixture is stirred for 16 hours at room temperature. The reaction mixture is then concentrated under reduced pressure and dissolved in 100 ml ethyl acetate and washed with water (2×30 ml). The organic phase is dried over MgSO4 and concentrated under reduced pressure. The residue is triturated in diisopropylether and pentane and dried under vacuum to yield 854 mg of 5-(5-chloro-6-methyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde. Yield=55%. Analytical LC/MS (method B): retention time=3.64 min, m/z=272.97 (1Cl, positive ion mode).

Provenance & Evidence