Category: 2451-91-4

Birkofer, Leonhard published the artcileRegularities in the hydrogenative fission of N-benzyl compounds, Recommanded Product: N,N-Dibenzylcyanamide, the publication is Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1942), 429-41, database is CAplus.

Because of the value of the preparative method of the catalytic removal of the N-CH₂Ph group, a study has been made of the influence of the residue on the N atom upon catalytic debenzylation. All hydrogenations were carried out at room temperature and atm. pressure in EtOH or AcOH, using PdO or PtO₂ as catalyst. PhCH₂NH₂, (PhCH₂)₂NH and PhCH₂NHMe are unchanged in the presence of PdO. (PhCH₂)₃N in AcOH (PdO) or its HCl salt in H₂O (PdO) gives 97% of (PhCH₂)₂NH.HCl; the amine is not reduced by Na and EtOH. Methylcetylbenzylamine in AcOH (PdO) gives 92% of cetylmethylamine-HCl and lauryldibenzylamine gives laurylmethylamine. Dodecyldibenzylamine in AcOH (PtO₂) gives 84% of dodecylhexahydrobenzylamine-HCl, m. 218°. (PhCH₂)₂NNH₂ in absolute EtOH (PdO) yields 88% of PhCH₂NHNH₂; tetrabenzyltetrazene [(PhCH₂)₂NN:]₂ gives (PhCH₂)₂NH. (PhCH₂)₃MeNOH with PdO in EtOH readily yields PhCH₂NHMe (flavianate, m. 190°; picrolonate, m. 210°), whereas (PhCH₂)₃MeNI is not reduced. PhCH₂NPhMe₂Cl gives 90% of cyclohexyldimethylamine. 2-Benzyldihydroisoindole in EtOH (PdO) yields 75% of 1,3-dihydroisoindole, b₃ 100°. 1,4-Dibenzylpiperazine in AcOH (PdO) gives 92% of piperazine diacetate, m. 234°. α-Monobenzylaminotetrazole gives aminotetrazole. PhCH₂NH₂ (1 mol.) in AcOEt is treated with a concentrated aqueous solution of 4 mols. of KCN and then dropwise with 1.1 mols. of Br in AcOEt at 5-10°, and the AcOEt solution shaken with 30% NaOH; the alkali removes the benzylcyanamide, which is polymerized to tribenzylisomelamine (1,3,5-tribenzyl-2,4,6-triimino-1,3,5-triazine) (I), m. 129-30°; short heating with HCl gives NH₃; with H and PdO in EtOH this yields melamine. The elimination of PhCH₂ from 2-imino-1-benzyl-1,2-dihydropyridine is slow and incomplete and is accompanied by nuclear hydrogenation, the products being 2-amino-3,4,5,6-tetrahydropyridine and 2-imino-1-benzylpiperidine (picrate, m. 106°). 2-Benzylaminopyridine does not lose PhCH₂ but is hydrogenated to 2-benzylamino-3,4,5,6-tetrahydropyridine, m. 40-1° (picrate, yellow, m. 131°; picrolonate, yellow, m. 199°). Aromatic rings, CO₂H and CN groups activate the compounds so that PhCH₂ is removed from a sec-N atom. PhNHCH₂Ph in EtOH (PdO) gives 97.5% of PhNH₂ and PhMe, whereas PtO₂ gives mainly cyclohexylhexahydrobenzylamine and small amounts of cyclohexylamine and hexahydrotoluene. PhN(CH₂Ph)₂ with PdO in EtOH gives 89% of PhNH₂ and PhMe. 2-(Dibenzylamino)naphthalene in AcOH (PdO) gives 88% of 2-C₁₀H₇NH₂ and PhMe. ClCH₂CO₂H (9 g.) and 40 g. (PhCH₂)₂NH in 20 cc. dioxane, heated 5 h. at 120°, give 82% of N,N-dibenzylglycocoll, m. 200°; Me ester, m. 41°; hydrogenation in AcOH (PdO) or in EtOH (PdO) gives NH₂CO₂H (95%) or its Me ester (96%). (PhCH₂)₂NCN yields NCNH₂ or I because of polymerization of PhCH₂NHCN if hydrogenation is interrupted before it is complete. (CONHCH₂Ph)₂ and N,N-dibenzylurethane, b₂ 169°, b₄ 181° (82% yield), are stable toward H.

Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Recommanded Product: N,N-Dibenzylcyanamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Bany, T. published the artcileChloroalkylamines, drugs paralyzing the endings of the sympathetic system, Name: N,N-Dibenzylcyanamide, the publication is Acta Poloniae Pharmaceutica (1955), 223-32, database is CAplus.

Derivatives of N,N-dibenzyl-β-chloroethylamine (Dibenamine) containing Br, I, or F and substituents other than benzyl are described as having possible paralyzing properties of the sympathetic system and action against malignant growth. FCH₂CH₂OH (I), b. 100-2°, was prepared in about 40% yield by adding with stirring 80 g. ClCH₂CH₂OH to a mixture of 87 g. KF (dried at 170°) and 110 g. HOCH₂CH₂OH heated at 210° at such a rate that a fraction b. 95-105° is distilled from the mixture, treating the distillate with 2 g. NaF, filtering and redistilling. FCH₂CH₂Cl (II), b₇₅₀ 57°, d₂₃ 1.1764, n_D²³ 1.3842 was obtained in 30% yield by adding 145 g. SOCl₂ to 60 g. I, refluxing 3 hrs. on a water bath, adding water, washing the resulting oil with NaHCO₃ and water, drying over CaCl₂ and distilling FCH₂CH₂Br (III), b₇₄₃ 72°, was obtained in a 23.7% yield by heating 7 g. I with 65 g. PBr₅ 3 hrs., washing the oil with water and Na₂CO₃, taking up in ether, drying and distilling (PhCH₂)₂NH.HCl (IV), not m. below 350°, was obtained by refluxing a mixture of 10 g. Na₂NCN, 45 g. water, 55 g. EtOH, and 25.2 g. PhCH₂Cl 36 hrs., distilling water and EtOH, crystallizing from petr. ether the resulting (PhCH₂)₂NCN, m. 112°, boiling it with 16 g. H₂SO₄ and 48 g. water 6 hrs., adding 26 g. NaOH in 48 g. water, steam distilling the amine, extracting the distillate with ether, treating the extract with HCl and filtering the precipitate (PhCH₂)₂NCH₂CH₂F.HCl (V), m. 248-50°, was prepared in 53% yield by heating 8 g. (PhCH₂)₂NH and 4 g. II in a sealed tube at 120-60° 24 hrs. and crystallizing from EtOH. (PhCH₂)₂NCH₂CH₂Br.HBr (VI), m. 181-2°, was obtained in 68% yield by adding HBr to 5 g. (PhCH₂)₂NCH₂CH₂OH (VII), filtering and drying the VII.HBr (m. 164°), heating it on a water bath 2 hrs. with 8.4 g. PBr₃ and 20 ml. CHCl₃, distilling the CHCl₃, adding EtOH, filtering the mixture, distilling the EtOH, and crystallizing from EtOH. Refluxing 6 g. VI and 5 g. NaI.2H₂O in 100 ml. AcOMe 2 hrs., evaporating to 0.5 volume, and cooling gave 7.2 g. (PhCH₂)₂NCH₂CH₂I.HI, m. 173-4° (from EtOH). (PhCH₂CH₂)₂NCH₂CH₂Cl.HCl (VIII), m. 153-4°, was obtained in 86.2% yield by refluxing 4 g. (PhCH₂CH₂)₂NCH₂CH₂OH in 20 ml. CHCl₃ with 2.5 g. SOCl₂ 4 hrs., removing CHCl₃, crystallizing the residue from EtOH-Et₂O and recrystallizing from AcOMe. (PhCH₂CH₂)₂NCH₂CH₂I.HI, m. 159-60°, was prepared in 85.7% yield by refluxing 1 g. VIII and 1.5 g. NaI.2H₂O in 25 ml. AcOMe 2 hrs., filtering off the precipitate, distilling the filtrate, taking up the residue in CHCl₃, filtering again, concentrating the filtrate and recrystallizing the solid from absolute EtOH. (α-C₁₀H₇CH₂)₂NCH₂CH₂Cl.HCl (IX), m. 185-6°, was prepared in 89.6% yield by refluxing 5 g. (α-C₁₀H₇CH₂)₂NCH₂CH₂OH and 2.7 g. SOCl₂ in 25 ml. CHCl₃ 4 hrs., distilling the CHCl₃, cooling, filtering off the precipitate, and crystallizing from absolute EtOH. (α-C₁₀H₇CH₂)₂NCH₂CH₂Br.HBr, m. 199-200°, was obtained in 82.5% yield by heating a solution of 1 g. IX in 5 ml. absolute EtOH with 1.2 g. CaBr₂.6H₂O in a min. quantity of absolute EtOH 6 hrs., cooling and recrystallizing from absolute EtOH. (α-C₁₀H₇CH₂)₂NCH₂CH₂I.HI, m. 181-2°, was obtained in 82.7% yield by heating 2 g. IX and 1.55 g. NaI.2H₂O in EtOH 8 hrs., cooling, filtering off the NaCl, concentrating the filtrate, and recrystallizing from MeOH. The piperidine derivative, C₅H₁₀NCH₂CH₂Cl.HCl (X), m. 234°, was obtained in 28.4% yield by heating on a water bath 13 g. C₅H₁₀NH with 12 g. ClCH₂CH₂OH 6 hrs., adding 50 ml. CHCl₃ and 23 g. SOCl₂, refluxing an addnl. 3 hrs., distilling the CHCl₃ and crystallizing from absolute EtOH. C₅H₁₀NCH₂CH₂Br.HBr, m. 219-20°, was obtained in 5.6% yield by refluxing 2 g. X and 2 g. CaBr₂.6H₂O in EtOH 6 hrs., distilling EtOH and crystallizing from AcOMe. C₅H₁₀NCH₂CH₂I.HI, m. 212-13°, was prepared in 5% yield by refluxing 2 g. X and 3 g. NaI.2H₂O in EtOH 6 hrs. and crystallizing from MeOH. C₅H₁₀NCH₂CH₂F.HCl (not m. below 350°) was prepared by heating 5 g. C₅H₁₀NH and 5 g. II 12 hrs. in a sealed tube at 140-60° and crystallizing from dilute EtOH.

Acta Poloniae Pharmaceutica published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Name: N,N-Dibenzylcyanamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Dubovtsev, Alexey Yu. published the artcileAcid-catalyzed [2+2+2] cycloaddition of two cyanamides and one ynamide: highly regioselective synthesis of 2,4,6-triaminopyrimidines, Quality Control of 2451-91-4, the publication is Organic & Biomolecular Chemistry (2021), 19(20), 4577-4584, database is CAplus and MEDLINE.

Triflic acid (10 mol%) catalyzes the highly regioselective [2+2+2] cycloaddition between two cyanamides and one ynamide to grant the 2,4,6-triaminopyrimidine core. The developed synthetic method is effective for the preparation of a family of the diversely substituted heterocyclic products (30 examples; yields up to 94%). The synthesis can be easily scaled up and conducted in gram quantities. As demonstrated by the post-functionalizations involving the amino-substituents, the obtained heterocycles represent a useful platform for the construction of miscellaneous pyrimidine-based frameworks. The performed d. functional theory calculations verified a particular role of H⁺, functioning as an electrophilic activator, in the regioselectivity of the cycloaddition

Organic & Biomolecular Chemistry published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Quality Control of 2451-91-4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Bonaga, Llorente V. R. published the artcileCobalt-mediated cyclotrimerization of bis-alkynes and cyanamides, Application of N,N-Dibenzylcyanamide, the publication is Chemical Communications (Cambridge, United Kingdom) (2004), 2394-2395, database is CAplus and MEDLINE.

CpCo(CO)₂-mediated cyclotrimerization of bis-alkynes and cyanamides provides multi-substituted (amino)pyridines, including macrocyclic products, in 50% yield. For example, the dicarbonyl(η⁵-cyclopentadienyl)cobaltate(1-)-catalyzed cyclotrimerization of di(2-propynyl)propanedioic acid di-Me ester (I) with 1-pyrrolidinecarbonitrile (II) gave (pyrrolidinyl)cyclopenta[c]pyridine-6,6-dicarboxylic acid (III).

Chemical Communications (Cambridge, United Kingdom) published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Application of N,N-Dibenzylcyanamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Chen, Zimin published the artcileN-Cyanation of Primary and Secondary Amines with Cyanobenziodoxolone (CBX) Reagent, Product Details of C15H14N2, the publication is Chemistry – A European Journal (2021), 27(60), 14836-14840, database is CAplus and MEDLINE.

An efficient electrophilic N-cyanation of amines e.g., pyrrolidine with a stable and less-toxic 1-cyano-1,2-benziodoxol-3-(1H)-one reagent towards the synthesis of cyanamides e.g., Pyrrolidine-1-carbonitrile was disclosed. This synthetically practicable strategy allows the construction of a wide variety of cyanamides under very mild and simple conditions with a broad functional group compatibility, and showcases a huge potential in late-stage modification of complex mols.

Chemistry – A European Journal published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Product Details of C15H14N2.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Teng, Fan published the artcileA copper-mediated oxidative N-cyanation reaction, COA of Formula: C15H14N2, the publication is Chemical Communications (Cambridge, United Kingdom) (2014), 50(61), 8412-8415, database is CAplus and MEDLINE.

Copper-promoted N-cyanation of aliphatic sec-amine by CuCN is achieved via oxidative coupling. This procedure employs O₂ as a clean oxidant. Notably, sulfoximines and 1,1,3,3-tetramethylguanidine also worked well in this procedure. Thus, it represents a key progress in the C-N bond formation reaction as well as in the cyanation reaction.

Chemical Communications (Cambridge, United Kingdom) published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C13H9FO2, COA of Formula: C15H14N2.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Savvina, L. N. published the artcileDibenzylamine, Formula: C15H14N2, the publication is Metody Polucheniya Khimicheskikh Reaktivov i Preparatov (1964), 28-9, database is CAplus.

Hydrolysis of (PhCH₂)₂NCN (I) with 40% H₂SO₄ yielded (PhCH₂)₂NH (II). A mixture of 68 ml. 40% H₂SO₄ and 0.1 mole I was heated 5 hrs. at 140°, cooled to 30-40°, 26 ml. 40% H₂SO₄ added, the mixture heated 3 hrs. at 140°, cooled, and ∼1 mole 40% NaOH added dropwise to weak alkalinity The oil was removed and the alk. solution extracted with CHCl₃ to yield 66-70% II, b. 298-300°.

Metody Polucheniya Khimicheskikh Reaktivov i Preparatov published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Formula: C15H14N2.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Savvina, L. N. published the artcileDibenzylcyanamide, COA of Formula: C15H14N2, the publication is Metody Polucheniya Khimicheskikh Reaktivov i Preparatov (1964), 32-3, database is CAplus.

(PhCH₂)₂– NCN (I) was synthesized from CaNCN and PhCH₂Cl (II). CaNCN (0.1 mole) was added to a mixture of 42 ml. H₂O and 10 g. ice, 0.2 mole 40% NaOH added after 30 min., the solution stirred 1 hr. at >25°, 0.02 mole II in 50 ml. alc. added, the mixture gently refluxed 3 hrs. unreacted II, alc., and oil were steam-distilled, the mixture was cooled to ∼20° and filtered, and the residue extracted with CHCl₃ to give 67.7-73.5% I, m. 47-50°.

Metody Polucheniya Khimicheskikh Reaktivov i Preparatov published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, COA of Formula: C15H14N2.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Tong, Peng published the artcileHydration of Nitriles to Amides by Thiolate-Bridged Diiron Complexes, Category: amides-buliding-blocks, the publication is Organometallics (2015), 34(14), 3571-3576, database is CAplus.

A series of nitrile-coordinating complexes [Cp*Fe(μ-SEt)RCN]₂[PF₆]₂ (1, R = alkyl, aryl, vinyl, amine) have been obtained by the reaction of [Cp*Fe(μ-SEt)MeCN]₂[PF₆]₂ (1a) with various nitriles in acetone. Complexes 1 can realize the hydration of a nitrile ligand under ambient conditions. Complexes [Cp*Fe(μ-SEt)₂(μ-η¹:η¹-NH(O)CR)FeCp*][PF₆] (2) were successfully isolated as intermediates during the hydration process, with 2b and 2e (R = CH₂:CH and Et₂N) being characterized by spectrometry and X-ray crystallog. Treatment of 2 with HBF₄·Et₂O in the presence of nitriles released corresponding amides 3. At the same time, the structural features of the [Fe₂S₂] scaffold were retained. These results confirmed that the hydration of nitriles was realized by cooperative interaction on diiron centers.

Organometallics published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C18H24N6O6S4, Category: amides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Zhu, Chen published the artcileA Simple Method for the Electrophilic Cyanation of Secondary Amines, Recommanded Product: N,N-Dibenzylcyanamide, the publication is Organic Letters (2014), 16(1), 247-249, database is CAplus and MEDLINE.

Bleach oxidizes trimethylsilyl cyanide to generate an electrophilic cyanating reagent that readily reacts with an amine nucleophile. This oxidative N-cyanation reaction allows for the preparation of disubstituted cyanamides from amines without using highly toxic cyanogen halides.

Organic Letters published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C14H10N2O, Recommanded Product: N,N-Dibenzylcyanamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics