4-Aminobenzonitrile → HCID 505532, compound

Participants

Reaction Steps

4,6-dichloro —N-(2,6-dibromo-4-methylphenyl)-1,3,5-triazin-2-amine (0.00651 mol), was dissolved in 1,4-dioxane (30 ml). Sequentially, 4-aminobenzonitrile (0.0066 mol) and N,N-diisopropylethylamine (0.0066 mol) were added, and the clear solution was heated to reflux for 4 days. The reaction was allowed to cool to room temperature overnight, and the mixture was diluted with ethyl acetate and treated with cold 1 M NaOH. The layers were separated, and the organic phase was re-extracted with fresh 1 M NaOH. The combined aqueous phases were treated with solid NaOH to maintain pH>10 and backwashed with ethyl acetate (2×). The combined organic phases were dried, filtered and concentrated. The residue was separated and purified by flash column chromatography over silica gel (eluent: CH2Cl2). The desired fractions were combined, treated with CH3CN, triturated with CH3CN, filtered off and dried, yielding 0.30 g (8.0%) of 4-[[4-amino-6-[(2,6-dibromo-4-methylphenyl)-amino]-1,3,5-triazin-2-yl]amino]benzonitrile.

Provenance & Evidence