94563-12-9

Upstream product

• 67-56-1 methanol 
• 23138-53-6 methyl 4-isocyanatobenzoate 
• 616-38-6 carbonic acid dimethyl ester 
• 619-45-4 4-methoxycarbonyl aniline 
• 6757-31-9 methyl-4-carbamoylbenzoate 
• 160852-85-7 2-[2-(2-methoxyethoxy)ethoxy]ethyl methyl carbonate 
• 79-22-1 methyl chloroformate 
• 20442-96-0 methyl 4-azidobenzoate 
• 103-71-9 phenyl isocyanate 

Downstream Products

• 30063-17-3 4-[(methoxycarbonyl)amino]benzoic acid 

Relevant academic research and scientific papers

PRODUCTION METHOD OF CARBAMIC ACID ESTER

A method of production of carbamic acid ester has a high yield and high selectivity and is superior in economy. The method of production of a carbamic acid ester includes reacting an amine, carbon dioxide, and an alkoxysilane compound in the presence of a catalyst containing a zinc compound or an alkali metal compound or in the presence of an ionic liquid. A carbamic acid ester is produced, for example by reacting aniline, carbon dioxide, and tetramethoxysilane at a temperature of 150 to 180° C. in the presence of zinc acetate and 2,2′-bipyridine.

Zr-MOF-808@MCM-41 catalyzed phosgene-free synthesis of polyurethane precursors

In this work, a catalytic method is presented for the synthesis of aromatic carbamates from aromatic amines using dimethyl carbonate instead of phosgene as a green and safe reaction process. Microcrystalline Zr-MOF-808 is reported as an active and efficient heterogeneous catalyst for the selective carbamoylation of anilines and industrially relevant aromatic diamines, under mild reaction conditions with near quantitative yields. We have accomplished the selective growth of well-dispersed Zr-MOF-808 nanocrystals within the mesoporous material MCM-41. A superior catalytic performance of the Zr-MOF-808@MCM-41 is demonstrated that together with increased stability stands out as an advantageous heterogeneous catalyst for polyurethane production. In situ FTIR studies have allowed a better understanding of the reaction pathway at the molecular level when the active MOF catalyst is present.

Electrochemical Hofmann rearrangement mediated by NaBr: Practical access to bioactive carbamates

An electrochemical Hofmann rearrangement is reported. With the mediation of NaBr, highly corrosive and toxic halogens are avoided. Moreover, this efficient and green approach is well compatible with a broad range of amides, including several commercial medicine derivatives, and provides direct access to synthetically useful carbamates. The synthetic utility of this method is also demonstrated by the preparation of 15N labeling carbamate and gram-scale synthesis of Amantadine.

A microfluidic flow chemistry platform for organic synthesis: the Hofmann rearrangement

We report on the use of commercially available chemical microreactors to effect the Hofmann rearrangement of aromatic amides to the corresponding carbamates. Crown Copyright

Selective N,N-dimethylation of primary aromatic amines with methyl alkyl carbonates in the presence of phosphonium salts

In the presence of onium salts, at 140-170 °C. methyl alkyl carbonates [1a-c, ROCO2Me, R = MeO(CH2)2[O(CH 2)2]n; n = 2-0, respectively] react with primary aromatic amines (XC6H4NH2, X = p-OMe, p-Me, H, p-Cl, p-CO2Me, o-Et, and 2,3-Me2C 6H3NH2) to yield the corresponding N,N-dimethyl derivatives (ArNMe2) with high selectivity (up to 96%) and good isolated yields (78-95%). Phosphonium salts (e.g., Ph3PEtI and n-Bu4PBr) are particularly efficient catalysts. Overall, a solvent-free reaction is coupled with safe methylating agents (1a-c) made from nontoxic dimethyl carbonate.

Design and synthesis of benzoic acid derivatives as influenza neuraminidase inhibitors using structure-based drug design

A series of 94 benzoic acid derivatives was synthesized and tested for its ability to inhibit influenza neuraminidase. The enzyme-inhibitor complex structure was determined by X-ray crystallographic analysis for compounds which inhibited the enzyme. The most potent compound tested in vitro, 5 (4- (acetylamino)-3-guanidinobenzoic acid), had an IC50 = 2.5 x 10-6 M against N9 neuraminidase. Compound 5 was oriented in the active site of the neuraminidase in a manner that was not predicted from the reported active site binding of GANA (4) with neuraminidase. In a mouse model of influenza, 5 did not protect the mice from weight loss due to the influenza virus when dosed intranasally.

Substituted benzene derivatives useful as neuraminidase inhibitors

A compound of the Formula (I): STR1 or pharmaceutically-suitable salts or prodrug forms thereof, wherein: n is 0-1; m is 0; p is 0-1; R1 is --CO2 H; R2 is selected from the group consisting of H, --OH, and --NH2 ; R3 is H; R4 is --C(O)NHR8 ; R5 is --NHC(R6)NH2 R6 is selected from the group consisting of =NH, =NOH, =NCN, =O, and =S; and R8 is selected from the group consisting of C1 -C4 linear or branched alkyl substituted with 0-3 halogens on each carbon.

Thermolysis of Aryl Azides in Phenyl Isocyanate

Aryl azides (p-XC6H4N3) decompose in boiling phenyl isocyanate to give mainly 1-phenyl-3-phenylcarbamoyl-2-oxo-1,3-dihydrobenzimidazoles and azo-compounds.In some cases, however (X=Ac, CO2Me, or CN) work-up in methanol solution produces methyl N-arylcarbamates (p-XC6H4NHCO2Me) indicative of the formation of substituted isocyanates (p-XC6H4NCO) during thermolysis.A mechanistic rationale is offered.