7335-35-5

Usage

Chemical Family

Urea family

Functional Groups

Urea group, hydroxyl group, and phenyl group

Usage

Intermediate in the synthesis of pharmaceuticals and agrochemicals

Primary Purpose

Building block in the production of new drugs and pesticides

Ongoing Research

Potential biological activities and therapeutic properties

Upstream product

• 103-71-9 phenyl isocyanate 
• 101-42-8 fenuron 
• 33026-77-6 N-(phenyl)-N'-phenylmethoxyurea 
• 1234457-71-6 C₁₁H₁₆N₂O₂ 
• 593-56-6 N-methoxylamine hydrochloride 
• 62-53-3 aniline 
• 49622-07-3 chloromethyl N-phenylcarbamate 

Downstream Products

• 70282-60-9 N-(tert-Butylsulfonyl)-N'-phenylharnstoff 
• 32380-80-6 N-(2-Hydroxybutyloxy)-N'-phenylharnstoff 
• 82255-38-7 C₁₅H₂₄N₂O₄ 
• 82255-32-1 C₁₅H₁₆N₂O₃ 
• 82255-39-8 C₂₃H₂₄N₂O₄ 
• 82255-33-2 C₁₃H₁₈N₂O₃ 
• 104308-38-5 3-(N-phenylcarbamoyl)-2-oxa-3-azabicyclo-<2.2.1>hept-5-ene 
• 104308-42-1 4,5-dimethyl-N-phenyl-3,6-dihydro-2H-1,2-oxazine-2-carboxamide 
• 2828-42-4 O-(Phenylcarbamoyl)acetonoxim 
• 82255-31-0 C₁₀H₁₄N₂O₃ 
• 82255-37-6 C₁₃H₂₀N₂O₄ 
• 96019-08-8 2-Phenoxy-succinic acid dimethyl ester 
• 79834-09-6 [2,5-Dioxo-1-phenyl-imidazolidin-(4Z)-ylidene]-acetic acid methyl ester 
• 603-54-3 N,N-diphenylurea 

Relevant academic research and scientific papers

1-methyl-1-methoxy-3-phenylurea synthetic method

The invention discloses a synthesis method of 1-methyl-1-methoxyl-3-phenylurea. The synthesis method comprises the following steps of carrying out gasification reaction of phenylamine and light in an organic solvent to obtain phenyl isocyanate; reacting an organic solvent solution of phenyl isocyanate with hydroxylamine sulphate in an alkaline aqueous solution in the presence of a catalyst A to obtain 1-hydroxyl-3-phenylurea; reacting 1-hydroxyl-3-phenylurea with dimethyl sulphate in the alkaline condition in the presence of a catalyst B to obtain 1-methyl-1-methoxyl-3-phenylurea. The synthesis method of 1-methyl-1-methoxyl-3-phenylurea has the advantages of being simple and direct in process, high in product purity, easy in control of production processes, and the like.

An Experimental and Computational Approach to Understanding the Reactions of Acyl Nitroso Compounds in [4 + 2] Cycloadditions

Catalytic aerobic oxidation of phenyl hydroxycarbamate 1 and 1-hydroxy-3-phenylurea 2 using CuCl2 and 2-ethyl-2-oxazoline in methanol gave acyl nitroso species in situ, which were trapped in nitroso-Diels-Alder (NDA) reactions with various dienes to afford the corresponding cycloadducts in high yields (90-98%). Competing ene products were also present for dienes containing both alkene π-bonds and allylic σ-bonds, and the ene yields are higher with 1 than with 2. The use of the chiral hydroxamic acid, (R)-1-hydroxy-3-(1-phenylethylurea) 3 (same conditions) gave NDA cycloadducts in high yields (97-99%) with no ene product from 2,3-dimethyl-1,3-butadiene. NDA cycloadducts were not obtained from other hydroxamic acid analogues [RCONHOH (R = PhCH2 4; Ph(CH2)2 5; Ph(CH2)3 6; Ph(CH2)4 7; Ph 8; 2-pyridyl 9; 3-pyridyl 10] with various dienes using copper-oxidation but rather were obtained using sodium periodate, resulting in variable NDA yields (13-51%) from hydroxamic acids 1-10 with cyclohexa-1,3-diene and 2,3-dimethyl-1,3-butadiene (several cycloadducts characterized by X-ray crystallography). The NDA and nitroso-ene reaction pathways of nitroso intermediates with dienes were mapped by DFT computations (B3LYP/6-31G), which showed that the acyl nitroso species are super-reactive and that activation energies in the NDA processes are lower than the isomerization barriers between some cis- and trans-butadienes.

Investigating N-methoxy-N′-aryl ureas in oxidative C-H olefination reactions: An unexpected oxidation behaviour

Herein, we report a urea derived directing group for mild and highly selective oxidative C-H bond olefination. Subsequent intramolecular Michael addition affords dihydroquinazolinones in good yields. The N-O bond of the urea substrate exhibits superior oxidative behaviour compared to a variety of other external oxidants. The Royal Society of Chemistry 2011.

Synthesis of substituted N-hydroxyureas via the in situ generation of t-butoxy isocyanate

Treatment of primary and secondary amines with tert- butylmesitylenesulfonoxycarbamate and a base afforded tert-butoxyurea, which when treated with an acid ultimately yielded substituted N-hydroxyureas. It is proposed that this proceeded via the generation of t-butoxy isocyanate in situ. This method allows for the synthesis of both mono and disubstituted N-hydroxyureas.

Analogues of N-hydroxy-N′-phenylthiourea and N-hydroxy-N′-phenylurea as inhibitors of tyrosinase and melanin formation

A series of N-hydroxy-N′-phenylthiourea and N-hydroxy-N′-phenylurea analogues were prepared and evaluated as inhibitors of tyrosinase and melanin formation. The most active analogue 1 inhibited mushroom tyrosinase with an IC50 of around 0.29 μM

A convenient method for the synthesis of N-hydroxyureas

Treatment of amines with 1-(4-nitrophenol)-N-(O-benzylhydroxy)carbamate yields the O-benzyl protected N-hydroxyureas. Hydrogenation of the O-benzyl protected N-hydroxyureas over 5% Pd/BaSO4 cleanly gives the N-hydroxyureas in good yield. In add

N-substituted hydroxyureas as urease inhibitors

In order to seek a urease inhibitor more potent than hydroxyurea (1), its alkyl- or phenyl-substituted derivatives were synthesized and evaluated for their effect on the jack bean urease. Of 16 compounds tested, m-methyl-(10) and m-methoxy-phenyl substituted hydroxyurea (13) showed the most potent inhibitory activities against the enzyme.

α-Haloalkyl Haloformates and Related Compounds 3.1 A Facile Synthesis of Symmetrical and Unsymmetrical Ureas via Chloromethyl Carbamates

Chloromethyl carbamates were prepared by the reaction of chloromethyl chloroformates with amines and found to produce mono-, symmetrically or unsymmetrically di- and trisubstituted ureas including their N-hydroxy and N-alkoxy derivatives in moderate to good yield.

Investigations of the Products of Isocyanates with Hydroxylamine

The reactions of isocyanates with hydroxylamine give rise to several compounds according to the different conditions involved when starting with the primary reaction products, the hydroxy-ureas.The pure compounds have been isolated.An interesting reaction of N-phenyl-N'-phenylcarbamoyloxyurea with sodium hydroxide has been observed.This compound is converted to 3-hydroxy-1,5-diphenylbiuret under conditions described.