Benzamidomethylation with (Benzamidomethyl)triethylammonium Chloride. 2. A Simple Method for Benzamidomethylation of Thiols, Amines and Carboxylic Acids

Popovski, Emil; Klisarova, Ljiljana; Vikić‐Topić, Dražen

doi:10.3390/50700927

Cited by 15 publications

(20 citation statements)

References 24 publications

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“…Mono(benzamidomethyl)hydroxylamine (3) was not obtained even when a two or three-fold excess of hydroxylamine was used. This phenomenon is comparable to our previous finding that primary amines give dibenzamidomethyl derivatives with 1 [3].…”

Section: Resultssupporting

confidence: 81%

“…Our previous research has shown that (benzamidomethyl)-triethylammonium chloride (1) is an excellent benzamidomethylating agent, both in non-aqueous and in aqueous media (pH > 9) [2,3]. We were especially interested in benzamidomethylation of phenols, thiols, amines and dithiocarbamates in aqueous media using 1, because of the mild reaction conditions, high yields and simple isolation of products [3]. In the course of this work, we have also carried out reactions of 1 with ammonia obtaining a mixture of di(benzamidomethyl)amine and tri(benzamido-methyl)amine [3].…”

Section: Introductionmentioning

confidence: 99%

“…Their properties have been thoroughly studied and they have been found to be superb phase-transfer catalysts in terms of stability, toxicity and cost [1]. Our previous research has shown that (benzamidomethyl)-triethylammonium chloride (1) is an excellent benzamidomethylating agent, both in non-aqueous and in aqueous media (pH > 9) [2,3]. We were especially interested in benzamidomethylation of phenols, thiols, amines and dithiocarbamates in aqueous media using 1, because of the mild reaction conditions, high yields and simple isolation of products [3].…”

Section: Introductionmentioning

confidence: 99%

“…We were especially interested in benzamidomethylation of phenols, thiols, amines and dithiocarbamates in aqueous media using 1, because of the mild reaction conditions, high yields and simple isolation of products [3]. In the course of this work, we have also carried out reactions of 1 with ammonia obtaining a mixture of di(benzamidomethyl)amine and tri(benzamido-methyl)amine [3]. Our intention was to further explore the reactions of 1 in aqueous media with other inorganic nucleophilic compounds.…”

Section: Introductionmentioning

confidence: 99%

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Reactions of (Benzamidomethyl)triethylammonium Chloride with Some Inorganic Nucleophiles in Aqueous Media

et al. 2006

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A variety of benzamidomethyl derivatives were prepared in water under alkaline conditions (pH>9) via reaction of (benzamidomethyl)triethylammonium chloride (1) with different inorganic nucleophiles. Reaction of 1 with hydroxylamine did not give the expected mono(benzamidomethyl)-hydroxylamine (3) but rather gave N,Ndi(benzamidomethyl)hydroxylamine (2). Reactions of 1 with sodium azide and potassium cyanide gave benzamidomethyl azide (4a) and benzamidomethyl cyanide (4b) respectively. Potassium thiocyanate and sodium iodide reacted with 1, and the anionexchanged products (benzamidomethyl)triethylammonium isothiocyanate (5a) and (benzamidomethyl)triethylammonium iodide (5b) were thus obtained. Cyanamide and potassium cyanate reacted readily with 1 and both gave the same mixture of di(benzamidomethyl)amine (7) and tri(benzamidomethyl)amine (8). All the reactions occurred smoothly, under mild conditions, to give the products in moderate to high yields.

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Section: Resultssupporting

confidence: 81%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Reactions of (Benzamidomethyl)triethylammonium Chloride with Some Inorganic Nucleophiles in Aqueous Media

et al. 2006

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“…[16][17][18][23][24][25] Of these, only L 3 and L 4 showed sufficient solubility in toluene in both the neutral and protonated forms to carry out studies of the extraction of chloridometalates. When L 1 was contacted with acidic zinc chloride solutions a third phase formed which prevented further analysis.…”

Section: Reagents and Conditionsmentioning

confidence: 99%

Outer-Sphere Coordination Chemistry: Amido-Ammonium Ligands as Highly Selective Tetrachloridozinc(II)ate Extractants

Turkington

Cocalia²,

Kendall

et al. 2012

Inorg. Chem.

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Eight new amido functionalized reagents, L 1 −L 8 , have been synthesized containing the sequence of atoms R 2 N−CH 2 −NR′−CO−R″, which upon protonation forms a six-membered chelate with a hydrogen bond between the tertiary ammonium N−H + group and the amido oxygen atom. The monocationic ligands, LH + , extract tetrachloridometal(II)ates from acidic solutions containing high concentrations of chloride ions via a mechanism in which two ligands address the "outer sphere" of the [MCl 4 ] 2unit using both N−H and C−H hydrogen bond donors to form the neutral complex as in 2L + 2HCl + MCl 2 ⇌ [(LH) 2 MCl 4 ]. The strengths of L 1 −L 8 as zinc extractants in these pH-dependent equilibria have been shown to be very dependent on the number of amide groups in the R 3-n N(CH 2 NR′COR″) n molecules, anti-intuitively decreasing with the number of strong hydrogen bond donors present and following the order monoamides > diamides > triamides. Studies of the effects of chloride concentration on extraction have demonstrated that the monoamides in particular show an unusually high selectivity for [ZnCl 4 ] 2over [FeCl 4 ] − and Cl − . Hybrid-DFT calculations on the tri-, di-, and monoamides, L 2 , L 3 , and L 4 , help to rationalize these orders of strength and selectivity. The monoamide L 4 has the most favorable protonation energy because formation of the LH + cation generates a "chelated proton" structure as described above without having to sacrifice an existing intramolecular amide−amide hydrogen bond. The selectivity of extraction of [ZnCl 4 ] 2over Cl − , represented by the process 2[(LH)Cl] + ZnCl 4 2-⇌ [(LH) 2 ZnCl 4 ] + 2Cl − , is most favorable for L 4 because it is less effective at binding chloride as it has fewer highly polar N−H hydrogen bond donor groups to interact with this "hard" anion.

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Nucleophilic substitution of the acetoxy group in 3-methylbenzoylaminomethyl acetate

et al. 2011

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Benzamidomethylation with (Benzamidomethyl)triethylammonium Chloride. 2. A Simple Method for Benzamidomethylation of Thiols, Amines and Carboxylic Acids

Cited by 15 publications

References 24 publications

Reactions of (Benzamidomethyl)triethylammonium Chloride with Some Inorganic Nucleophiles in Aqueous Media

Reactions of (Benzamidomethyl)triethylammonium Chloride with Some Inorganic Nucleophiles in Aqueous Media

Outer-Sphere Coordination Chemistry: Amido-Ammonium Ligands as Highly Selective Tetrachloridozinc(II)ate Extractants

Nucleophilic substitution of the acetoxy group in 3-methylbenzoylaminomethyl acetate

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