17101-98-3

Upstream product

• 541-41-3 chloroformic acid ethyl ester 
• 104-84-7 para-methylbenzylamine 
• 6132-45-2 ethyl 4-nitrophenyl carbonate 
• 22719-86-4 1-(4-ethoxycarbonyloxy-phenyl)-ethanone 
• 22719-89-7 ethyl m-nitrophenyl carbonate 
• 64-17-5 ethanol 
• 622-47-9 4-tolylacetic acid 
• 263746-53-8 O-ethyl-S-(4-bromophenyl)thiocarbonate 
• 78725-88-9 O-ethyl S-(4-methylphenyl) thiocarbonate 
• 107701-35-9 O-ethyl S-(4-chlorophenyl) thiocarbonate 
• 78725-90-3 S-phenyl-O-ethyl thiolcarbonate 

Downstream Products

• 41789-95-1 1-(3-methoxyphenyl)-N-methylmethanamine 
• 699-04-7 N-methyl-p-methylbenzylamine 

Relevant academic research and scientific papers

Urethanes synthesis from oxamic acids under electrochemical conditions

Urethane synthesis via oxidative decarboxylation of oxamic acids under mild electrochemical conditions is reported. This simple phosgene-free route to urethanes involves an in situ generation of isocyanates by anodic oxidation of oxamic acids in an alcoholic medium. The reaction is applicable to a wide range of oxamic acids, including chiral ones, and alcohols furnishing the desired urethanes in a one-pot process without the use of a chemical oxidant.

The design and synthesis of 9-phenylcyclohepta[d]pyrimidine-2,4-dione derivatives as potent non-nucleoside inhibitors of HIV reverse transcriptase

Novel compounds, which can be considered as conformationally restricted analogues of MKC-442, have been synthesized and tested as inhibitors of the reverse transcriptase of human immunodeficiency virus type-1 (HIV-1). Reaction of urea with a β-ketoester furnished 6,7,8,9-tetrahydro-9-phenyl-1H- cyclohepta[d]pyrimidine-2,4-(3H,5H)-dione (6a) and 6,7,8,9-tetrahydro-9-p-tolyl- 1H-cyclohepta[d]pyrimidine-2,4-(3H,5H)-dione (6b) which were then alkylated at the N-1 position with chloromethyl ether, allyl bromide and benzyl bromide to afford the target compounds 7a-b, 8a-b, 9 and 10, respectively. The seven-membered, annelated compounds have a relatively rigid structures and can lock the orientation of the aromatic ring. Chemical modification at N-1 of the pyrinidine ring and the 9-phenyl ring was attempted, with the aim of improving the antiretroviral activity. In particular, replacement of the aliphatic group with the phenyl moiety at the terminus of N-1 side chain can enhance the activity. The most active compounds showed activity in the low micromolar range with IC50 values comparable to that of nevirapine. The biological activity results are in accordance with the docking results. The Royal Society of Chemistry 2006.

Preparation and applications of a polymer-supported phosphoryl azide

A polymer-supported diphenylphosphoryl azide was prepared. This polymer-supported version of DPPA is useful due to its lower toxicity, moisture tolerance and ease of workup after reaction. The synthetic application of this solid-phase reagent was explored by conversion of a variety of carboxylic acids to urethanes and ureas through Curtius rearrangement reactions. Carboxylic acids bearing different functional groups (aromatic, aliphatic and heterocyclic carboxylic acids) were subjected to the reaction. The corresponding products were isolated with satisfactory yields.

Kinetics and mechanism of the aminolysis of O-ethyl S-aryl thiocarbonates in acetonitrile

The Kinetics and mechanism of the reactions of O-ethyl S-(Z)aryl thiocarbonates with (X)benzylamines in acetonitrile at 45.0 °C are studied. Relatively small values of βx (βnuc) = 0.6 to approximately 0.8 and βz (βlg) = -0.5 to approximately -0.7 together with a negative cross-interaction constant ρxz (= -0.47) and failure of the reactivity-selectivity principle (RSP) are interpreted to indicate a concerted mechanism. The normal kinetic isotope effects (kH/kD = 1.3 to approximately 1.8) involving deuterated benzylamine nucleophiles suggest a hydrogen-bonded, four-center-type transition state.

Kinetics and mechanism of the aminolysis of ethyl aryl carbonates in acetonitrile

The aminolysis reactions of ethyl aryl carbonates with benzylamines in acetonitrile at 25.0°C are investigated. The base-catalyzed path, k2, disappears when strong nucleophiles (X = p-CH3O and p-CH3) react with a substrate activated by a strong nucleofuge (Z = p-NO2). The large magnitude of ρ(x) (-1.7 to -2.5), ρ(z) (3.4 to 4.3), and ρ(xz) (1.4) values, and relatively large k(H)/k(D) (1.6 to 1.8) found for the uncatalyzed path (k1) can be accounted for in terms of a stepwise mechanism with rate-limiting expulsion of the phenoxide leaving group. The catalyzed process (k2) is characterized by the much smaller magnitude of ρ(x) (-1.0 to -1.7), ρ(z) (0.4 to 0.7), and ρ(xz) (0.2), the larger k(H)/k(D) (2.1 to 2.5) values, and the lower ΔH(+) values (1.8-1.9 kcal mol-1) than those of the uncatalyzed process (k1) with large negative ΔS(+) values (-65 to -67 cal K-1 mol- 1). These results are consistent with four- and six-centered transition states for the two processes, k1 and k2, respectively.

Preparation of urethanes by oxidative carbonylation of amines using copper carboxylates as oxidants

A process for preparing urethanes by reacting a primary or secondary amine with carbon monoxide, an alcohol, a catalytic quantity of a compound or complex of palladium, platinum or rhodium and a stoichiometric quantity of a copper(II) salt of a monocarboxylic acid. When the amine is aromatic, the process is conducted in the presence of a selected Lewis base promoter and a compound or complex of palladium.