4-Iodo-o-toluidine → 4-Chloro-2-(1H-tetrazol-5-yl)-(4-iodo-2-methyl-phenyl)-amine

Participants

Reaction Steps

To a solution of 2-methyl-4-iodoaniline (3.52 g, 0.0151 mol) in THF (25 mL) at −78° C., LDA (2 molar solution in THF, 11.33 mL, 0.02267 mol) was added dropwise. After stirring for 0.5 hours, a solution of 1-(tetrazol-5-yl)-2-fluoro-5-chlorobenzene (1.5 g, 0.00756 mol) in THF (15 mL) was added dropwise. The reaction was stirred for 16 hours as it warmed up to room temperature. The reaction mixture was quenched with aqueous conc. NH4Cl solution and extracted with CH2Cl2. The organic layer was dried (MgSO4) and the solvent removed giving a crude product as an oil. The oil with CH2Cl2->CH2Cl2:MeOH (9.7:0.3) gave 1.5 g (48%) of the desired product:

Provenance & Evidence