Ammonia → HCID 19086710, compound

Participants

Reaction Conditions

Reaction Steps

2-cyano-5-(2-chloro-4-trifluoromethyl-6-fluorophenoxy)-1H-benzimidazole-3-oxide (0.8 g) was suspended in chloroform (5cm3) stirred and cooled to 5° C. in an ice bath. Phosphorus trichloride (0.25cm ) was added dropwise and when addition was complete the mixture was heated under reflux for 5 minutes. The resulting solution was cooled, water (10cm3) added slowly and the mixture made basic with aqueous ammonia. The organic layer was separated and the aqueous layer extracted twice with chloroform. The combined organic phase was washed with water, dried (MgSO4), filtered and the filtrate evaporated under vacuum. A portion of the residue was purified by preparative plate chromatogrpahy (SiO2 ; ether) to give 2-cyano-5-(2-chloro-4-trifluormethyl-6-fluorophenoxy)benzimidazole as a pale yellow solid, recrystallised from ether/hexane. MS (positive FAB) MH+ =356.

Provenance & Evidence