《Ethyl 2-Cyano-2-(2-Nitrophenylsulfonyloximino)Acetate (ortho-NosylOXY) Mediated One-Pot Racemization Free Synthesis of Ureas, Carbamates, and Thiocarbamates via Curtius Rearrangement》 was written by Kalita, Tapasi; Dev, Dharm; Mondal, Sandip; Giri, Rajat Subhra; Mandal, Bhubaneswar. Synthetic Route of C7H5IO2This research focused onurea preparation; carbamate preparation; thiocarbamate preparation; carboxylic acid ethyl cyano nitrophenylsulfonyloximino acetate Curtius rearrangement. The article conveys some information:
A detailed NMR-based mechanism study is incorporated here. Direct conversion of to ureas RNHC(O)NHR1 (R = Ph, 4-methylphenyl, 4-methoxybenzyl, (tert-butoxycarbonylamino)(phenyl)methyl, etc.; R1 = 4-chlorophenyl, tert-Bu, methoxycarbonylmethyl, etc.), carbamates RNHC(O)OR1 (R = 4-methoxyphenyl, 4-bromophenyl; R1 = 4-nitrobenzyl, 4-methoxybenzyl), and thiocarbamate RNHC(O)SR1 (R = Ph, undecan-1-yl, 2-methoxyphenyl; R1 = 4-chlorobenzyl) in a single pot via Curtius rearrangement is accomplished. One recently established coupling reagent, ethyl-2-cyano-2-(2-nitrophenylsulfonyloximino)acetate (ortho-NosylOXY), is successfully used for the racemization free synthesis of ureas, di-peptidyl ureas, and carbamates with moderate to good yield (82-69%). This single-pot hassle-free procedure works with a diverse range of N-protecting groups Fmoc, Boc, and Cbz. Various amines R1NH2, including aromatic, Me esters of amino acids, tert-butylamine, benzyl alcs. (such as 4-nitrobenzyl alc., 4-methoxybenzyl alc.), and (4-chlorophenyl)-methanethiol, are used as nucleophiles. Racemization suppression, easy removal of byproducts, and less waste generation make this methodol. useful. The experimental process involved the reaction of 4-Iodobenzoic acid(cas: 619-58-9Synthetic Route of C7H5IO2)
4-Iodobenzoic acid(cas: 619-58-9) belongs to organic iodides. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Synthetic Route of C7H5IO2Iodo alkanes participate in a variety of organic synthesis reactions, which include the SimmonsSmith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com