92550-15-7

Usage

InChI:InChI=1/C15H14Cl2N2O/c16-13-5-1-11(2-6-13)9-18-15(20)19-10-12-3-7-14(17)8-4-12/h1-8H,9-10H2,(H2,18,19,20)

Upstream product

• 42275-64-9 2,2,2-Trichloro-N-(4-chloro-benzyl)-acetamide 
• 201230-82-2 carbon monoxide 
• 104-86-9 4-chlorobenzylamine 
• 868-84-8 S,S-dimethyl dithiocarbonate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 67-56-1 methanol 
• 13278-62-1 1-(4-chlorobenzyl)-3-methylurea 
• 14062-24-9 4-chloro-benzeneacetic acid, ethyl ester 
• 108-90-7 chlorobenzene 
• 55718-52-0 1,1'-((4-chlorophenyl)methylene)diurea 
• 90346-91-1 N-Nitroso-N-methyl-N'-(4-chlor-benzyl)-harnstoff 
• 115601-14-4 4-Chlorphenylacetylazid 
• 57676-51-4 2-(4-chlorophenyl)acetic hydrazide 

Downstream Products

• 60285-27-0 N-Nitroso-N,N'-bis-(4-chlor-benzyl)-harnstoff 
• 67-56-1 methanol 
• 104-86-9 4-chlorobenzylamine 
• 42365-43-5 (4-chlorophenyl)methanamine hydrochloride 

Relevant academic research and scientific papers

Method for preparing symmetric urea compound

The invention provides a novel reaction system for synthesizing a symmetric urea compound by taking CO2 as a carbonylation reagent, wherein Lewis base and hydrosilane are used as accelerators and efficiently enable an aromatic/aliphatic primary amine compound to react with normal-pressure CO2 to generate corresponding symmetric urea compounds containing different functional groups under mild conditions (100 DEG C, diglyme). According to the method, normal-pressure CO2 is used as an environmentally-friendly non-toxic carbonylation reagent, and cheap Lewis base and PMHS (industrial silicon waste) are used as accelerators, so that the use of toxic carbonylation reagents, isocyanate, high-pressure CO2, expensive dehydrating agents and precious metals is avoided, purification and separation ofintermediates are not needed, pure products can be obtained only through simple suction filtration and separation after the reaction is finished, and the method is an efficient and novel synthesis method and has high industrial application value.

Effective approach to ureas through organocatalyzed one-pot process

An efficient approach to N, N′-unsymmetrically substituted ureas 9 has been developed through the ammonolysis process of N-Boc protected anilines 7 with amines prompted by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). Moreover, a convenient protocol for the

Ruthenium-Catalyzed Urea Synthesis Using Methanol as the C1 Source

An unprecedented protocol for urea synthesis directly from methanol and amine was accomplished. The reaction is highly atom-economical, producing hydrogen as the sole byproduct. Commercially available ruthenium pincer complexes were used as catalysts. In addition, no additive, such as a base, oxidant, or hydrogen acceptor, was required. Furthermore, unsymmetrical urea derivatives were successfully obtained via a one-pot, two-step reaction.

NaIO4-oxidized carbonylation of amines to ureas

Oxidative carbonylation of amines using NaIO4 as the oxidant and NaI as a promoter affords good to excellent yields of ureas from primary amines in the absence of transition metal catalysts. The Royal Society of Chemistry 2009.

Preparation of mono-, di-, and trisubstituted ureas by carbonylation of aliphatic amines with S,S-dimethyl dithiocarbonate

General procedures are reported to prepare N-alkylureas, N,N′-dialkylureas (both symmetrical and unsymmetrical), and N,N,N′-trialkylureas by carbonylation of aliphatic amines, employing S,S-dimethyl dithiocarbonate (DMDTC) as a phosgene substitute. All reactions were carried out in water. Symmetrical disubstituted ureas were prepared directly working at 60°C with a molar ratio of DMDTC:amine = 1:2, preferably under nitrogen. Unsymmetrical ureas were prepared in two steps via S-methyl N-alkyl-thiocarbamate intermediates, which are formed selectively in the first step at room temperature. These intermediates react in the second step with ammonia or various aliphatic amines, both primary and secondary, at temperatures varying between 50 and 70°C. All the target ureas were obtained in high yields (28 examples, average yield 94%) and with very high purity (generally >99.2%). Also to be noted is the recovery of a co-product of industrial interest, methanethiol, in an amount of two moles for each mole of DMDTC, with complete exploitation of the reagent. Georg Thieme Verlag Stuttgart.

W(CO)6-catalyzed oxidative carbonylation of primary amines to n,n'-disubstituted ureas in single or biphasic solvent systems. Optimization and functional group compatibility studies

Primary amines undergo carbonylation to N,N'-disubstituted ureas using W(CO)6 as the catalyst, I2 as the oxidant, and CO as the carbonyl source. Preparation of various N,N'-disubstituted ureas from aliphatic primary amines, RNH2 (R = n-Pr, n-Bu, i-Pr, sec-Bu, or t-Bu), was achieved in good to excellent yields. Studies of functional group compatibility using a series of substituted benzylamines demonstrated broad tolerance of functionality during the carbonylation reaction. Preparation of various N,N'-disubstituted ureas from substituted benzylamines, R-C6H4CH2NH2 (R = H, p-OCH3, p-CO2H, p-CO2Et, p-CH2OH, p-SCH3, p-vinyl, p-Cl, p-Br, m-I, p-NH2, p-NO2, or p-CN), was achieved in good yields. For many substituted benzylamines, yields of ureas were higher when a two-phase CH2Cl2/H2O solvent system was used.

UREAS IN ORGANIC SYNTHESIS IX. REACTION OF ARYLMETHYLENEBISUREAS WITH SODIUM BOROHYDRIDE - A SINGLE-STAGE PATH TO SYMMETRICAL DIBENZYLUREAS

Symmetrical dibenzylureas are formed when arylmethylenebisureas are boiled with sodium borohydride in alcohol.The reaction of benzylidenebisurea with sodium borohydride in DMFA at 160 deg C gives mainly perhydro-2-phenyl-1,3,5-triazine-4,6-dione.

NEW PROCEDURES FOR THE SYNTHESIS OF SYMMETRICAL BISBENZYLATED UREAS BASED ON N-BENZYLTRICHLOROACETAMIDES

Treatment of N-benzylated trichloroacetamides 4, obtained by three different procedures, with potassium carbonate in dimethylsulfoxide affords simmetrical bisbenzylated ureas 5.