𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Facile and Selective Synthesis of 4-Methyl- and 4-Phenylthiosemicarbazide (=N-Methyl- and N-Phenylhydrazinecarbothioamide) Derivatives of Benzil (=1,2-Diphenylethane-1,2-dione)

✍ Scribed by David G. Calatayud; Francisco J. Escolar; Elena López-Torres; M. Antonia Mendiola

Publisher
John Wiley and Sons
Year
2007
Tongue
German
Weight
593 KB
Volume
90
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

A selective synthesis of 4‐methylthiosemicarbazide (=N‐methylhydrazinecarbothioamide; 4a) derivatives by reaction with benzil (=1,2‐diphenylethane‐1,2‐dione; 3) is described. The reaction conditions determined the condensation product formed. The most important factor was the acid used: in the presence of conc. HCl solution, the open‐chain 2 : 1 compound 1a was exclusively obtained, whereas in the presence of 2M HCl, the cyclic 1 : 1 condensation product 2a was formed. The alcohol used, the presence of H~2~O, and the time of heating were additional crucial factors. The new cyclic compound 2a with a MeO group was exclusively formed when working under high‐dilution conditions. The reaction with the 4‐phenyl derivative 4b gave new cyclic compounds as the major products under all conditions used (Scheme).

📜 SIMILAR VOLUMES

Synthesis and structures of 6-methyl-1-(
Synthesis and structures of 6-methyl-1-(2-R-phenyl)-dihydropyrimidine-2,4-dione derivatives
✍ R. S. Baltrushis; V. Yu. Mitskyavichyus; I. Ch. Bilinskaite; R. M. Zolotoyabko; 📂 Article 📅 1990 🏛 Springer US 🌐 English ⚖ 892 KB

N.Aryl.f-methyl-~-alanines were synthesized by the reaction of aromatic amines with crotonic acid. The products were converted to dihydropyrimidine-2,4-dione derivatives. Alkylation, acylation, and oximation of l-arylpyrimidine-2,4-diones were carried out. Conformational analysis of the compounds ob

High nitrogen chemistry: Synthesis and p
High nitrogen chemistry: Synthesis and properties of N,N-bis(4,5-dicyano-1-methyl-2-imidazolyl)cyanamide and N,N,N′,N′,N″,N″-hexakis(4,5-dicyano-1-methyl-2-imidazoly)melamine
✍ Ramachandran P Subrayan; Paul G Rasmussen 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 355 KB

Cyanation of bis(4,5-dicyano-l-methyl-2-imidazolyl)arnine(1) using cyanogen chloride gave N,N-bis(4,5-dicyano-l-methyl-2-imidazolyl)cyanamide(3) as a light yellow solid. Compound 3 is themmlly labile and upon heating the N-CN bond is cleaved and the reactive amine intermediate readily reacts with th