Garbrecht, William L.’s team published research in Journal of Organic Chemistry in 18 | CAS: 2451-91-4

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.

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°, n20D 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°, n23D 1.4670. Other R2NCN prepared are: R = Bu, b35 147-51°, n20D 1.4382; iso-Bu, b25 123°, n20D 1.4346; iso-Am, b14 134°, n20D 1.4405; PhCH2, b10 145-8°, m. 54°; Me, PhCH2, b12 139-42°, n20D 1.5297; Et, PhCH2, b12 160°, n20D 1.5223; 1-cyanopiperidine, b11 102°, n25D 1.4678; 4-cyanomorpholine, b15 117-19°, n25D 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