Trifluoromethylsulfonamide → HCID 18315509, compound

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Reaction Steps

N,N′-carbonyldiimidazole (0.647 g) is added all at once to an N,N-dimethylformamide (20 ml) solution of 6-carboxy-1-(2-chlorobenzyl)-2-methylbenzimidazole (0.600 g) (example 75), and the solution is stirred for one hour at room temperature. Subsequently, an N,N-dimethylformamide (5 ml) solution of trifluoromethanesulfonamide (0.596 g) and diazabicycloundecene (0.609 g) is added, and the solution is stirred for 72 hours at 100° C. The reaction solution is cooled and the solvent is removed through evaporation under reduced pressure. Water and ethyl acetate are added to the residue. While being stirred, 10% hydrochloric acid is added until the aqueous layer became acidic. Precipitated crystals are washed with a mixture solvent of ethanol (25 ml) and methanol (25 ml). The crystals are dried and thus, 1-(2-chlorobenzyl)-2-methyl-6-trifluoromethanesulfonylcarbamoylbenzimidazole hydrochloride (214) (0.420 g) is obtained. 1H-NMR (DMSO-d6, δ): 2.84 (3H, s), 5.82 (2H, s), 7.08 (1H, d, J=7.5 Hz), 7.30 (1H, t), 7.40 (1H, t, J=7.7 Hz), 7.58 (1H, d, J=8.0 Hz), 7.79 (1H, d, J=8.6 Hz), 8.07-8.13 (2H, m).

Provenance & Evidence