22671-74-5

Usage

Chemical class

Urea derivatives

Synthesis method

Reaction of 1-butylisocyanate and p-toluidine

Physical state

White solid

Solubility in water

Sparingly soluble

Solubility in organic solvents

Soluble

Potential applications

Pharmaceuticals, agrochemicals, and materials science

Utility

Reagent in organic synthesis

Possible biological activities

Investigated for potential therapeutic uses

Upstream product

• 106-49-0 p-toluidine 
• 111-36-4 n-butyl isocyanide 
• 33275-26-2 N-(4-methylphenyl)-O-phenyl carbamate 
• 109-73-9 N-butylamine 
• 104-87-0 4-methyl-benzaldehyde 
• 3235-02-7 p-methylbenzaldehyde oxime 
• 36288-37-6 N-hydroxy-4-methylbenzenecarboximidoyl chloride 
• 1536471-98-3 N-butyl 4-methylbenzamidoxime 
• 7625-64-1 p-tolyl-carbamic acid benzyl ester 
• 124-38-9 carbon dioxide 
• 37934-96-6 2,2,2-trichloroethyl N-p-tolylcarbamate 
• 2318-82-3 N-hydroxy-4-methylbenzamide 
• 2769-64-4 n-butyl isonitrile 
• 622-58-2 p-Tolylisocyanate 

Relevant academic research and scientific papers

Lanthanum(III) Trifluoromethanesulfonate Catalyzed Direct Synthesis of Ureas from N-Benzyloxycarbonyl-, N -Allyloxycarbonyl-, and N -2,2,2-Trichloroethoxycarbonyl-Protected Amines

A novel lanthanum triflate mediated conversion of N -benzyloxycarbonyl-, N -allyloxycarbonyl-, and N -trichloroethoxycarbonyl-protected amines into nonsymmetric ureas was discovered. In this study, lanthanum triflate was found to be an effective catalyst for preparing various nonsymmetric ureas from protected amines. A variety of protected aromatic and aliphatic carbamates reacted readily with various amines in the presence of lanthanum triflate to generate the desired ureas in high yields. This result demonstrated that this novel lanthanum triflate catalyzed preparation of ureas from Cbz, Alloc, and Troc carbamates can be employed for the formation of various urea structures.

Metal-Free Synthesis of Unsymmetrical Ureas and Carbamates from CO2 and Amines via Isocyanate Intermediates

A mild and metal-free synthesis of aryl isocyanates from arylamines under an atmosphere of CO2 was developed. The carbamic acid intermediate, derived from the arylamine starting material and CO2 in the presence of DBU, is dehydrated by activated sulfonium reagents to generate the corresponding isocyanate. The latter can be detected by in situ IR and trapped by various amines and alcohols to make unsymmetrical ureas and carbamates, respectively. Dicarbamates can also be prepared in good yields via the mild dehydration of the corresponding dicarbamic acids.

Practical synthesis of N -substituted cyanamides via tiemann rearrangement of amidoximes

A facile and general synthesis of various N-substituted cyanamides was accomplished by the Tiemann rearrangement of amidoximes with benzenesulfonyl chlorides (TsCl or o-NsCl) and DIPEA.

Lossen rearrangements under heck reaction conditions

The classical Lossen rearrangement converts activated hydroxamic acids to isocyanates that form numerous products upon their reaction with nucleophiles. We report a simple and highly efficient method of using Heck reaction conditions to initiate Lossen rearrangements of hydroxamic acids. In addition, Lossen rearrangements occur in the presence of palladium(II) acetate or triethylamine, components of the Heck reaction, alone. A potential mechanism is provided to explain this reactivity and these results show that Heck reactions and Lossen rearrangements occur under the same conditions and may provide new methods for facile initiation of Lossen rearrangements.

Synthesis of multisubstituted pyrroles from doubly activated cyclopropanes using an iron-mediated oxidation domino reaction

An alternative route has been developed for the construction of multisubstituted pyrrole derivatives from readily available, doubly activated cyclopropanes and anilines using an iron-mediated oxidation domino reaction (i.e., sequential ring-opening, cyclization, and dehydrogenation reactions). This reaction uses readily available reactants and is tolerant of a broad range of substrates, with the desired products being formed in good to excellent yields.

Cobalt(II)-catalyzed isocyanide insertion reaction with amines under ultrasonic conditions: A divergent synthesis of ureas, thioureas and azaheterocycles

Cobalt(II) acetylacetonate-catalyzed isocyanide insertion reactions with amines utilizing tert-butyl hydroperoxide (TBHP) as an oxidant under ultrasound conditions have been developed, which lead to the synthesis of ureas, thioureas, as well as 2-aminoben

Phenyl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylate as carbonyl source: Facile and selective synthesis of carbamates and ureas under mild conditions

The selective syntheses of carbamates, symmetric -ureas, and unsymmetrical ureas have been accomplished by the -reaction of amines with phenyl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylate as a carbonyl source under mild conditions. It is noteworthy that this process is mild, economic, and convenient.

Relative binding affinity of carboxylate and its isosteres: Nitro, phosphate, phosphonate, sulfonate, and δ-lactone

Using the mono and ditopic receptors 1 and 2 (N-n-butyl-N′-p-tolylurea and 4,8-bis[((n-butylamino)carbonyl)amino]dibenz[b, i]acridan), the relative binding affinities of the title functional groups were determined to be ArOPO32- ≥ ArPO32- > ArCOO- ≥ ArP(OH)O2- > ArOP(OH)O2- > ArSO3- > δ-lactone > ArNO2. No evidence of hydrogen bonding of nitrobenzene to 1 was detected in either CDCl3 or DMSO-d6, but in CCl4, Kassoc = 180 M-1. Ditopic receptor 2 was designed as a receptor for meta-disubstituted aromatic substrates and binds some (isophthalate and 1,3-C6H4(P(OH)O2-)2) with high affinity (Kassoc > 104 M-1) in DMSO-d6. In contrast, the isosteric m-dinitrobenzene is not bound by 2 in that solvent, which further illustrates the relatively poor hydrogen bonding ability of nitro groups.

KINETICS OF REACTIONS OF para-SUBSTITUTED PHENYL ISOCYANATES WITH AMINES AND ALCOHOLS

The reaction of para-substituted phenyl isocyanates with amines and alcohols was studied by stopped-flow method.The Hammett correlation obtained showed that the sensitivity of the above mentioned reactions toward substituent effects is the same as that of