Category: 2451-91-4

Mukaiyama, Teruaki published the artcileThe effects of substituents on the hydrolysis of substituted cyanamides in sulfuric acid solution, Category: amides-buliding-blocks, the publication is Bulletin of the Chemical Society of Japan (1954), 416-21, database is CAplus.

The following RR’NCN were prepared either from RR’NH and BrCN, or (where R and R’ are the same) from the corresponding halide and Na₂NCN [R, R’, b.p. (mm.) given, resp.]: Et, H, 94-5° (4); Bu, H, 117° (14); n-heptyl, H, nondistillable; iso-Pr, H, 108° (10); tert-Bu, H, 109-10° (11); allyl, H, 92° (3); Ph, H, -, m. 42°; Et, Et, 78° (16); Bu, Bu, 120-1° (16); iso-Pr, iso-Pr, 93-4° (25); allyl, allyl, 107-8° (18); PhCH₂, PhCH₂, m. 53.5°. The hydrolysis of 0.1M solutions of the RR’NCN in 3:1 dioxane-water containing 20% by weight of H₂SO₄ was followed kinetically by contraction in volume, measured with a dilatometer. All of the ureas thus produced were known compounds except N,N-diallylurea, m. 64° (from petr. ether). Tables of rate constants at different temperatures, activation energies, and entropies of activation are given for hydrolysis of the various cyanamides. The rate of reaction increases in the series: (iso-Pr)₂, Et₂, Ph, tert.-Bu, H₂, iso-Pr, Et, heptyl. From these results it is proposed that the rate-determining step in the hydrolysis mechanism is the protonation of the cyanamide bisulfate, RR’NC(:NH)OSO₃H, which is in turn dependent upon the basic strength of the cyanamide. This hypothesis is not in accord with the mechanism proposed by Kilpatrick (C.A. 41, 1916g).

Bulletin of the Chemical Society of Japan 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, Category: amides-buliding-blocks.

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

Jonczyk, Andrzej published the artcileReactions of organic anions; LXXXV. Catalytic two-phase alkylation of cyanamide, Name: N,N-Dibenzylcyanamide, the publication is Synthesis (1978), 882-3, database is CAplus.

R₂NCN (R = PhCH₂, H₂C:CHCH₂, Bu, Et, Me₂CHCH₂CH₂, Me₂CH, Me, MeOCH₂, BuOCH₂) were prepare by reaction of H₂NCN with RX (X = Cl, Br) in presence of Aliquat 336. The heterocycles I [Q = (CH₂)_n, n = 2, 3, 4; o-C₆H₄] were similarly prepared from H₂NCN and BrCH₂QCH₂Br.

Synthesis 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

Cardona, Raymond A. published the artcileReactions of (triphenylstannyl)carbodiimides and-cyanamide with organic halides and isothiocyanates, Name: N,N-Dibenzylcyanamide, the publication is Journal of Organometallic Chemistry (1972), 43(1), 163-73, database is CAplus.

The reaction of bis(triphenylstannyl)carbodiimide (I) with alkyl halides was not a general route to dialkyl-carbodiimides. I and trityl chloride gave ditritylcarbodiimide, but I and PhCH2Br gave a dibenzylcyanamide-Ph3SnBr complex (II). The reaction of N-(triphenylstannyl)-N -tritylcarbodiimide (III) with trityl chloride also afforded ditritylcarbodiimide, but the reaction of III with PhCH2Br gave a benzyltritylcyan-amide-Ph3SnBr complex (IV). The complexes (II) and (IV) were prepared also from Ph3SnBr and dialkylcyanamides. Some evidence that the nitrile N, rather than the amino N, is bonded to Sn in these complexes was found. The reaction of (triphenylstannyl)cyanamide (V) with trityl chloride andEt3N gave di-tritylcarbodiimide and a small amount of III. The reaction of I with PhNCO gave N-phenyl-N -(triphenylstannyl)-N -cyano-S-(triphenylstannyl)isothiourea. V and organic isothiocyanates gave N-substituted N -cyano-S-(triphenylstannyl)isothioureas. The order of reactivity of organic isothiocyanates in this reaction was determined N-Phenyl-N -cyano-S-(triphenylstannyl)isothiourea decomposed in refluxing C6H6 to give bis(triphenyltin) sulfide and a 1,3,5-thiadiazine derivative

Journal of Organometallic 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, Name: N,N-Dibenzylcyanamide.

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

Schroth, Werner published the artcileDehydration of ureas with dichlorocarbene in the phase transfer method, Computed Properties of 2451-91-4, the publication is Zeitschrift fuer Chemie (1981), 21(1), 25-7, database is CAplus.

Mono- and disubstituted ureas RR¹NCONH₂ [R = alkyl, R¹ = H, alkyl, or Ph; R = R¹ = PhCH₂; or RR¹ = (CH₂)₄, (CH₂)₅, oxydiethylene, or (phenylimino) diethylene] were dehydrated by treatment with :CCl₂ in the presence of a phase-transfer catalyst, (PhCH₂)Et₃NCl, to give 20-85% RR¹NCN. (CH₂)₄NCSNH₂ was obtained in 45% yield by the addition of H₂S to (CH₂)₄NCN in the presence of an equimolar amount of dry Et₃N.

Zeitschrift fuer Chemie 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, Computed Properties of 2451-91-4.

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

Schroth, W. published the artcileThe dehydration of ureas by two-phase dichlorocarbene reaction, a synthetic access to substituted cyanamides, Category: amides-buliding-blocks, the publication is Journal fuer Praktische Chemie (Leipzig) (1983), 325(5), 787-802, database is CAplus.

A wide variety of N,N-disubstituted ureas were dehydrated in the CHCl₃/NaOH catalytic 2-phase system under mild conditions. The sequence of urea transamidation and dehydration offers a profitable approach to aprotic cyanamides. Among various phase-transfer catalysts tertiary amines prove to be the most efficient. Tertiary amines may also be used in the transformation of carboxamides and thioamides to the corresponding nitriles. The application of the same technique is less suitable in the case of N-monosubstituted ureas, N,N‘-disubstituted ureas, and N-(dialkylaminomethylene)ureas, since subsequent reactions of the cyanamides predominate. The dehydration mechanism is elucidated in terms of HOMO-perturbation theory.

Journal fuer Praktische Chemie (Leipzig) 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, Category: amides-buliding-blocks.

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

Hashimoto, Toru published the artcileIridium-Catalyzed [2+2+2] Cycloaddition of α,ω-Diynes with Cyanamides, Application In Synthesis of 2451-91-4, the publication is Advanced Synthesis & Catalysis (2015), 357(18), 3901-3916, database is CAplus.

The complex [Ir(cod)Cl]₂/DPPF or rac-BINAP is an efficient catalyst for the [2+2+2] cycloaddition of α,ω-diynes with cyanamides. A wide range of cyanamides derived from secondary amines are good coupling partners for α,ω-diynes. The reaction of unsym. α,ω-diynes possessing two different internal alkyne moieties with cyanamides is regioselective. A competitive experiment showed that cyanamide is more reactive than nitrile. This higher reactivity of cyanamide than nitrile was analyzed based on d. functional theory (DFT) calculations at the B3LYP level.

Advanced Synthesis & Catalysis 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 In Synthesis of 2451-91-4.

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

Suzuki, K. published the artcileBenzylation of guanidine by phase transfer reaction, Recommanded Product: N,N-Dibenzylcyanamide, the publication is Research Reports of the Faculty of Engineering, Tokyo Denki University (1996), 39-49, database is CAplus.

Phase transfer reaction was studied to apply to the synthesis of substituted guanidines, especially highly alkyl-substituted guanidines. The reaction produced 27 weight% N, N, N’, N’, N”-pentabenzylguanidine using tetra-butylammonium hydrogen sulfate as catalyst. The reaction and byproduct formation mechanism are proposed.

Research Reports of the Faculty of Engineering, Tokyo Denki University 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 C5H10O2S, Recommanded Product: N,N-Dibenzylcyanamide.

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

Garbrecht, William L. published the artcileThe synthesis of certain 5-aminotetrazole derivatives. I. The action of hydrazoic acid on some dialkylcyanamides, Name: N,N-Dibenzylcyanamide, the publication is Journal of Organic Chemistry (1953), 1003-13, database is CAplus.

A number of 5-dialkylaminotetrazoles, HN.N:N.N:C-NR₂ (I), are prepared to be tested for their pharmacol. activity by the interaction of R₂NCN and HN₃ in polar and non-polar solvents. R₂NCN are prepared by 2 methods: (A) 12 cc. Br in 40 cc. Skellysolve B is added dropwise to 32 g. Am₂NH and 59 g. KCN in 60 cc. H₂O with vigorous stirring at 0°, giving 88% Am₂NCN, b₁₂ 154-8°, n²⁰_D 1.4422; (B) 53 g. BrCN in ether is added (2 h.) to 71 g. pyrrolidine in ether with cooling and stirring, giving 58% 1-cyanopyrrolidine, b₁₇ 107-10°, n²³_D 1.4670. Other R₂NCN prepared are: R = Bu, b₃₅ 147-51°, n²⁰_D 1.4382; iso-Bu, b₂₅ 123°, n²⁰_D 1.4346; iso-Am, b₁₄ 134°, n²⁰_D 1.4405; PhCH₂, b₁₀ 145-8°, m. 54°; Me, PhCH₂, b₁₂ 139-42°, n²⁰_D 1.5297; Et, PhCH₂, b₁₂ 160°, n²⁰_D 1.5223; 1-cyanopiperidine, b₁₁ 102°, n²⁵_D 1.4678; 4-cyanomorpholine, b₁₅ 117-19°, n²⁵_D 1.4708. Adding (1.5 h.) 250 cc. concentrated H₂SO₄ to 520 g. NaN₃ in 500 cc. H₂O and 1.5 l. C₆H₆ with stirring and cooling, and drying the C₆H₆ layer with Na₂SO₄ give a stock solution containing 15-17 g. HN₃/100 cc. Adding HN₃ from 33 g. NaN₃ in 100 cc. H₂O to 39 g. Bu₂NCN in 200 cc. 95% EtOH gives 85% I (R = Bu), fine needles, m. 132.5-3.5°. Refluxing 80 g. Me(PhCH₂)NCN in 200 cc. xylene containing 32 g. HN₃ 5 h., adding another 100 cc. HN₃ solution, and refluxing another 18 h. give 89% I (R = Me and PhCH₂), fine needles, m. 135.5-6.5° [HCl salt, needles, decompose 179° (sealed tube)]. Refluxing 10 g. (iso-Am)₂NCN with 35 cc. xylene containing 4.5 g. HN₃ 22 h. and, after addition of another 35 cc., another 67 h. gives 9.8 g. I (R = iso-Am), needles, m. 100-1°. Refluxing 6.3 g. Pr₂NCN and 4.2 g. NH₃ in 100 cc. EtOH and 50 cc. H₂O 65 h. gives 39% I (R = iso-Pr), existing in 2 forms, m. 162.5-3.5° and 184° (decomposition). The following addnl. I are prepared [R, solvent used, time (hrs.), % yield, and m.p. in the order given]: Me (II), aqueous EtOH, 5.5, 78, 235-6°; Et, aqueous EtOH, 6, 43, 124-5°; allyl, aqueous EtOH, 17.5, 36 (EtOAc, 20, 58), 96-7°; Bu, aqueous EtOH, 15, 85, 132.5-3.5° (HCl salt, plates, decompose 183°); iso-Bu, aqueous EtOH, 14, 91, 190-1°; Am, aqueous EtOH, 24, 87, 91.5-2.5°; PhCH₂, aqueous EtOH, 46, 91, 158-9°; Et and PhCH₂, xylene, 57, 88, 134.5-5°; piperidino, aqueous EtOH, 43, 79 (C₆H₆, 25, 85), 199-9.5°; morpholino, C₆H₆, 23, 78, 180.5-1°; 1-pyrrolidinyl, aqueous EtOH, 26, 54 (C₆H₆, 23, 86), 231° (decomposition). The Ag salts are prepared by treating I in EtOH with aqueous AgNO₃ solution The apparent dissociation constants and equivalent weights of I in 50% MeOH were determined and the UV absorption curves of I (R = H), II, and some related compounds are described.

Journal of Organic 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, Name: N,N-Dibenzylcyanamide.

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

Keil, Dietmar published the artcileA simple route to N,N-disubstituted selenoureas from N,N-disubstituted cyanamides, Application In Synthesis of 2451-91-4, the publication is Synthesis (2004), 15-16, database is CAplus.

N,N-Disubstituted selenoureas I [R¹ = R² = Me, Et, Bn; R¹R² = O(CH₂CH₂)₂, (CH₂)₅, (CH₂)₄] can be obtained in good yields by addition of an acid to a mixture of freshly prepared sodium selenide and N,N-disubstituted cyanamides II.

Synthesis 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 In Synthesis of 2451-91-4.

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

Keil, Dietmar published the artcilePreparation and characterization of N,N-disubstituted 2-amino-selenazoles, Recommanded Product: N,N-Dibenzylcyanamide, the publication is Phosphorus, Sulfur and Silicon and the Related Elements (1999), 169-184, database is CAplus.

As a result of checking suited methods for preparing N,N-disubstituted 2-amino-selenazoles, e.g. I, as a nearly unknown class of highly reactive selenazoles a simple route starting from N,N-disubstituted selenoureas has been elaborated and used for the synthesis of a series of these compounds The necessary selenium-containing starting compounds N,N-disubstituted selenoureas are available from N,N-disubstituted cyanamides and hydrogen selenide.

Phosphorus, Sulfur and Silicon and the Related Elements 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