A simple and efficient procedure for the synthesis of benzimidazoles using air as the oxidant

Tetrahedron Letters

Volumn 46, Issue 25, 2005, Pages 4315-4319

  Lin, Songnian ^a   Yang, Lihu ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Air oxidation; Aldehydes; Benzimidazoles; Green chemistry; Heterocycle; Mild conditions; Simple procedure

Indexed keywords

ALDEHYDE; BENZIMIDAZOLE; OXIDIZING AGENT; PHENYLENEDIAMINE; WATER;

AIR; ARTICLE; DEHYDROGENATION; DRUG SYNTHESIS; PURIFICATION; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

EID: 19544370229     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.04.101     Document Type: Article

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42. General procedure: A solution of 3,4-diaminotoluene (0.25 mmol) and benzaldehyde (0.25 mmol) in 1 mL of solvent or neat was placed in a 50 mL capped tube. The tube was flushed with air, capped, and heated for 4 h at refluxing or at 100°C (see Table 1). The reaction mixture was then cooled to room temperature, and diluted to 10 mL with methanol. The crude mixture was then analyzed by a reverse-phase HPLC using a 0.025 M methanol solution of 3,4-diaminotoluene and a 0.025 M methanol solution of 2-phenyl-5- methylbenzimidazole as the standards
43. 8a)
44. 2/MeOH = 15:1) to afford the desired benzimidazole
45. In some cases, small amounts (<5%) of bis-Schiff's bases resulting from the condensation of one equivalent of diamines with two equivalents of aldehydes were observed
46. +)