5532-90-1

Usage

InChI:InChI=1/C10H13NO2/c1-2-8-13-10(12)11-9-6-4-3-5-7-9/h3-7H,2,8H2,1H3,(H,11,12)

Upstream product

• 71-23-8 propan-1-ol 
• 55-21-0 benzamide 
• 201230-82-2 carbon monoxide 
• 586-96-9 Nitrosobenzene 
• 67-56-1 methanol 
• 64-17-5 ethanol 
• 1202047-15-1 1-tert-butyl-1-ethyl-3-phenylurea 
• 103-71-9 phenyl isocyanate 
• 62-53-3 aniline 
• 590-28-3 potassium cyanate 
• 98-80-6 phenylboronic acid 
• 3087-37-4 titanium tetra-n-propoxide 
• 124-38-9 carbon dioxide 
• 582-61-6 benzoyl azide 

Downstream Products

• 71-23-8 propan-1-ol 
• 103-71-9 phenyl isocyanate 

Relevant academic research and scientific papers

N-Aryl and N-Alkyl Carbamates from 1 Atmosphere of CO2

We have successfully isolated and characterized the zinc carbamate complex (phen)Zn(OAc)(OC(=O)NHPh) (1; phen=1,10-phenanthroline), formed as an intermediate during the Zn(OAc)2/phen-catalyzed synthesis of organic carbamates from CO2, amines, and the reusable reactant Si(OMe)4. Density functional theory calculations revealed that the direct reaction of 1 with Si(OMe)4 proceeds via a five-coordinate silicon intermediate, forming organic carbamates. Based on these results, the catalytic system was improved by using Si(OMe)4 as the reaction solvent and additives like KOMe and KF, which promote the formation of the five-coordinated silicon species. This sustainable and effective method can be used to synthesize various N-aryl and N-alkyl carbamates, including industrially important polyurethane raw materials, starting from CO2 under atmospheric pressure.

Nickel-Catalyzed Synthesis of N-(Hetero)aryl Carbamates from Cyanate Salts and Phenols Activated with Cyanuric Chloride

A simple and efficient domino reaction has been designed and employed for the one-pot synthesis of N-(hetero)aryl carbamates through the reaction between alcohols and in-situ produced (hetero)aryl isocyanates in the presence of a nickel catalyst. The phenolic C?O bond was activated via the reaction of phenol with cyanuric chloride (2,4,6-trichloro-1,3,5-triazine (TCT)) as an inexpensive and readily available reagent. This strategy provides practical access to N-(hetero)aryl carbamates in good yields with high functional groups compatibility.

Visible-Light-Promoted Oxo-Sulfonylation of Ynamides with Sulfonic Acids

A visible-light-promoted oxo-sulfonylation of ynamides with sulfonic acids is reported, giving rise to a collection of functionalized α-sulfonylated amides in a straightforward manner. The reaction proceeds sequentially through a cascade of electrophilic addition and photoinduced sulfonyl radical-sustained skeleton rearrangement. The high atom economy, mild reaction conditions, and wide substrate scope comprised the merits of this synthetic transformation.

A Fe3O4?SiO2/Schiff Base/Pd Complex as an Efficient Heterogeneous and Recyclable Nanocatalyst for One-Pot Domino Synthesis of Carbamates and Unsymmetrical Ureas

A palladium-catalyzed domino method for the direct synthesis of carbamates and ureas has been developed by using readily available and economical starting materials (aryl halide, carbon monoxide, sodium azide, amines and alcohols) in a one-pot approach. The domino process underwent carbonylation, Curtius rearrangement, and nucleophilic addition. This protocol provides a step-economical and highly efficient reaction to access the wide range of valuable carbamates, symmetrical and unsymmetrical ureas with high yields under remarkable mild reaction conditions that are important factors in pharmaceutical science, biochemistry and agricultural industries. Furthermore, the magnetically recoverable nanocatalyst (Fe3O4?SiO2/Pd(II)) can be conveniently and swiftly recycled using external magnet and reused at least for seven times without noticeable loss of its catalytic activity.

Carbon dioxide utilization in the efficient synthesis of carbamates by deep eutectic solvents (DES) as green and attractive solvent/catalyst systems

A green and eco-friendly solvent/catalyst system based on a deep eutectic solvent (DES) was devised and developed for the simple synthesis of carbamates through three-component coupling of amines, alkyl halides and carbon dioxide (CO2). It was found that choline chloride:zinc(ii) chloride ([ChCl][ZnCl2]2) was very proficient and effective for the activation and utilization of CO2 in carbamate formation reactions from a wide scope of amines. Surprisingly, this strategy provides the desired carbamates under atmospheric CO2 pressure at room temperature. In particular, both aromatic and aliphatic amines were effective and demonstrated excellent yields. Besides, the [ChCl][ZnCl2]2 exhibited very high stability and also could be reused for at least five consecutive cycles without any significant loss of activity. It is worth noting that this is the first solvent/catalyst system which can be recycled successfully from the reaction mixture.

An Fe3O4@SiO2/Schiff base/Cu(ii) complex as an efficient recyclable magnetic nanocatalyst for selective mono: N-arylation of primary O-alkyl thiocarbamates and primary O-alkyl carbamates with aryl halides and arylboronic acids

An efficient, convenient and novel method for the selective mono N-arylation of primary O-alkyl thiocarbamates and primary O-alkyl carbamates with aryl halides and arylboronic acids in the presence of a recyclable magnetic Cu(ii) nanocatalyst is described. A variety of mono N-arylated O-alkyl thiocarbamates and O-alkyl carbamates were prepared in good to excellent yields with a broad range of aryl coupling partners. The magnetic nanocatalyst can be easily recovered with an external magnetic field and reused at least five times without noticeable leaching or loss of its catalytic activity. This cost-effective and eco-friendly methodology has some other advantages, such as easy preparation of the catalyst, simple workup procedure, and easy purification, which makes this protocol interesting for the users in various fields of pharmacology and biotechnology systems.

Ureas as safe carbonyl sources for the synthesis of carbamates with deep eutectic solvents (DESs) as efficient and recyclable solvent/catalyst systems

A simple, efficient and eco-friendly one-pot synthesis of primary, N-mono- and N-disubstituted carbamates is developed from ureas. The corresponding carbamates were produced at 120 °C, within 18 h, and in the presence of a deep eutectic solvent as a recyclable catalytic system. The catalyst can be reused for several runs without any reduction in its activity. To demonstrate the utility of this approach, a wide variety of alcohols and phenols were studied to find a vast range of carbamate derivatives in moderate to high yields.

An efficient one-pot synthesis of N,N′-disubstituted phenylureas and N-aryl carbamates using hydroxylamine-O-sulfonic acid

We have developed an efficient one-pot method for the microwave-assisted synthesis of ureas and carbamates via a proposed Lossen rearrangement. Herein we report the first examples of the direct conversion of benzoyl chlorides into N,N′-disubstituted ureas and N-aryl carbamates using hydroxylamine-O-sulfonic acid as reagent. Using our general method, we have produced 11 examples of N,N′-disubstituted phenylureas in yields up to 95% using various substituted anilines, and primary and secondary amines. Additionally, we were able to generate a series of N-aryl carbamates in moderate yields using primary, secondary and tertiary alcohols.

Direct Catalytic Synthesis of N-Arylcarbamates from CO2, Anilines and Alcohols

The direct catalytic synthesis of carbamates from CO2, amines and methanol was achieved by controlling both the reaction equilibrium and the reactivity of the three components. The combination of CeO2 and 2-cyanopyridine was an effective catalyst, providing various carbamates including N-arylcarbamates in high selectivities.

METHOD FOR PRODUCING CARBAMATE

PROBLEM TO BE SOLVED: To provide a method for producing carbamate in which a high yield can be obtained and the amount of by-products produced can be reduced. SOLUTION: In the method, carbamate is synthesized using at least one member selected from the group consisting of amine and derivative thereof, alcohol having 3 or more carbon atoms and carbon dioxide as a raw material, cerium oxide as a catalyst, and 2-cyanopyridine as a dehydrating agent. By using an alcohol having 3 or more carbon atoms, a high yield can be obtained and the amount of by-products produced can be reduced. In addition, the pressure of carbon dioxide can be lowered and the production can be of ease. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2018,JPO&INPIT