Sodium Hydroxide Catalyzed <i>N</i>‑Alkylation of (Hetero) Aromatic Primary Amines and N₁,C₅‑Dialkylation of 4‑Phenyl-2-aminothiazoles with Benzyl Alcohols

In the presence of a catalytic amount of NaOH, the selective N-alkylation of various heteroaromatic primary amines is reported. With 1 equiv of NaOH, N1,C5-dialkylation of 4-phenyl-2-aminothiazoles has been investigated. Reaction of in situ generated aldehyde with amine yields the N-alkylated and N1,C5-dialkylated products through hydride ion transformation from alcohol.