Trifluoroacetic acid → HCID 11517942, compound

Participants

Reaction Steps

To a magnetically stirred solution of tert-butyl 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfonyl-1H-imidazole-4-carboxylate (4.76 g, 9.49 mmol) in CH2Cl2 (60 ml) was added excess TFA (9.40 ml, 0.2124 mol) and Et3SiH (3.8 ml, 0.0238 mol). The solution was reacted at room temperature for 16 h and concentrated in vacuo. Water was added and the formed precipitate was collected by filtration and subsequently dried to give 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfonyl-1H-imidazole-4-carboxylic acid in quantitative yield, mp ˜130° C. (dec); 1H-NMR (400 MHz, CDCl3) δ 3.45 (s, 3H), 3.50 (br s, 1H), 7.40 (br d, J˜8 Hz, 2H), 7.42 (dd, J=8 and 2 Hz, 1H), 7.50 (br d, J˜8 Hz, 2H), 7.59 (d, J=2 Hz, 1H), 7.61 (d, J=8 Hz, 1H). Analogously was prepared 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfinyl-1H-imidazole-4-carboxylic acid 1H-NMR (400 MHz, CDCl3) δ 2.99 (s, 3H), 7.37-7.60 (m, 7H), 13.20 (br s, 1H).

Provenance & Evidence