Toluene → 5,6-dichloro-N-isopropyl-1H-benzo[d]imidazol-2-amine

Participants

Reaction Conditions

Reaction Steps

5,6-Dichloro-1,2-phenylenediamine (0.61 g, 3.4 mmol), and isopropyl isothiocyanate (0.39 g, 3.8 mmo) were combined in anhydrous pyridine (10 mL) and were heated to 80° C. for 15 min. Dicyclohexylcarbodiimide (1.06 g, 5.14 mmol) was then added and the resulting mixture was allowed to stir at 100° C. for 5 h. Toluene (30 mL) was added and the mixture was concentrated by rotary evaporation leaving a brown residue. The product was flilrer purified by silica gel chromatography using 6.5:3:0.5 ethyl acetatelhexane/triethylamine to afford a gummy solid which was recrystallised from acetonitrile to give 0.46 g (60%) of a tan solid; m.p. 218-220° C. Anal. Calcd for C10H11Cl2N3 : C, 49.20; H, 4.54; N, 17.21. Found: C. 49.31; H, 4.59; N, 17.33.

Provenance & Evidence