13599-69-4

Usage

InChI:InChI=1/C14H13NO2/c1-15(12-8-4-2-5-9-12)14(16)17-13-10-6-3-7-11-13/h2-11H,1H3

Upstream product

• 4285-42-1 N-phenyl-N-methylcarbamoyl chloride 
• 100-67-4 potassium phenolate 
• 108-95-2 phenol 
• 1885-14-9 phenyl chloroformate 
• 100-61-8 N-methylaniline 
• 874-52-2 N,N-dimethylaniline N-oxide 
• 121-69-7 N,N-dimethyl-aniline 
• 3416-49-7 N-butyl-N-methylaniline 
• 92289-43-5 imidazole-1-carboxylic acid methylphenylamide 

Relevant academic research and scientific papers

Synthesis of highly condensed heterocycles using radical reactions

Using radical chemistry novel highly condensed heterocycles have been synthesized. The mechanism for their formation is discussed.

A new protocol for the formation of carbamates and thiocarbamates using carbamoyl imidazolium salts

Carbamoyl imidazolium salts are demonstrated to act as useful carbamoylation reagents, in reactions with alcohols, phenols, thiols and thiophenols to form carbamates and thiocarbamates under relatively mild conditions. The salts are stable and easily prepared from the corresponding amines using CDI.

Efficient demethylation of N,N-dimethylanilines with phenyl chloroformate in ionic liquids

Demethylation of N,N-dimethylanilines was carried out in various ionic liquids and acetonitrile as well as under solvent-free conditions. We have demonstrated that their reactivity dramatically depends on the ionic liquid employed; [bmim]Cl showed the bes

Carbamoylimidazolium and thiocarbamoylimidazolium salts: Novel reagents for the synthesis of ureas, thioureas, carbamates, thiocarbamates and amides

Carbamoylimidazolium salts act as efficient N,N-disubstituted carbamoylating reagents. These salts are readily prepared by the sequential treatment of secondary amines with N,N′-carbonyldiimidazole (CDI) and iodomethane. The carbamoylimidazolium salts are more efficient carbamoyl transfer reagents than the intermediate carbamoylimidazoles, as a result of the 'imidazolium' effect. Kinetic studies on the base promoted hydrolysis of both carbamoylimidazoles and carbamoylimidazolium salts reveal over a hundred-fold rate acceleration. The salts react with amines, thiols, phenols/alcohols, and carboxylic acids in high yields, without the need for subsequent chromatographic purification of the products, producing ureas, thiocarbamates, carbamates, and amides, respectively. Analogous thiocarbamoylimidazolium salts were also synthesized from secondary amines and N,N′-thiocarbonyldiimidazole (TCDI), followed by methylation with iodomethane.

Mild and selective deprotection of carbamates with Bu4NF

A new mild method allowing the removal of carbamates using TBAF in THF is reported. Reactions were performed on indole, indoline, N-methyl aniline, aniline and tryptamine derivatives. The observed selectivity according to the carbamates or the substrates is discussed. A mechanism is postulated. Graphical Abstract

Silicon Polonovski Reaction. Formation and Synthetic Application of α-Siloxy Amines

A new and versatile synthetic intermediate, α-siloxy amine was prepared in situ by the base-promoted rearrangement of a siloxyammonium salt obtained by treatment of a tertiary amine N-oxide with trialkylsilyl trifluoromethanesulfonate.The best combination of the base and silylating reagent was found to be methyllithium and t-butyldimethylsilyl trifluoromethanesulfonate.The reactions of α-siloxy amines with acyl halides and haloformates gave the corresponding amides and carbamates in moderate to good yields, respectively.Treatment of α-siloxy amines with acetic acid resulted in a direct dealkylation to free secondary amines.Fluoride induced alkylation of α-siloxy amines using alkyl halides as electrophiles leading to tertiary amines was also examined and demonstrated to be a new transalkylation method of amines.