Benzotriazole-1-carboxamidinium Tosylate: An Alternative Method for the Conversion of Amines to Guanidines

Simple generalized reaction conditions for the conversion of primary aliphatic amines to surfactant-like guanidine salts with 1H-pyrazole carboxamidine hydrochloride

“…C NMR (100 MHz, d4-MeOH): 157.2 (NH-C=NH), 41.1 (-CH2-NH-), 31.1, (-CH2-CH2-NH-), 28.5, 26.0, 22.2, 12.9 (-CH3) ppm. NMR spectra is similar to spectra of the tosylate salt of the same compound synthesized by Katritzky et al14 Synthesis of 2b:General procedure B lead to 2b as an oil (94 mg, 0.45 mmol, 59% yield). 1 H NMR (400 MHz, d4-MeOH): δ = 3.16 (t, 2H, J = 7.0 Hz, -CH2-NH-), 1.58 (p, 2H, J = 7.1 Hz, -CH2-CH2-NH-), 1.43 -1.25 (m, 10H, 5 x CH2), 0.91 (t, 3H, J = 7.0 Hz, CH3) ppm 13.…”

Five‐Membered Heterocycles with Three Heteroatoms: Triazoles

“…For example, benzotriazole-1-carboxamidinium tosylate (102) was found to be an efficient reagent for the synthesis of mono-and disubstituted guanidines 103 in moderate to good yields and offers advantages over previous procedures (Table 12.14) [162]. Introduction of Boc groups on both nitrogens of the amidine moiety and nitro or chloro group on the benzotriazole enhances the ability of the benzotriazole moiety as a leaving group [163].…”

Recent developments in guanylating agents

“…In a recent, one-pot procedure, quaternary ammonium permanganate in the presence of amine showed advantages over other oxidizing agents for thioureas 120 52 (Scheme 43, Table 33). 53 prepared from benzotriazole 128 with cyanamide 127 in refluxing 1,4-dioxane in the presence of p-TsOH, is an efficient general reagent for the synthesis of mono and disubstituted guanidines 130. Reactions are conveniently carried out using equimolar amine in (i) DMF-diisopropylethylamine at room temperature, (ii) acetonitrile or (iii) the absence of solvent.…”