4773-33-5

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 3626, 1948 DOI: 10.1021/ja01191a026Organic Syntheses, Coll. Vol. 4, p. 169, 1963

InChI:InChI=1/C10H11ClO2/c1-2-13-10(12)9(11)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3/t9-/m0/s1

Upstream product

• 64-17-5 ethanol 
• 4755-72-0 Chloro-phenyl-acetic acid 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 5317-66-8 ethyl α,α-dichlorophenylacetate 
• 2912-62-1 α-chlorophenylacetyl chloride 
• 7719-09-7 thionyl chloride 
• 60-29-7 diethyl ether 
• 611-71-2 MANDELIC ACID 
• 121-44-8 triethylamine 
• 50916-31-9 2-hydroxy-2-phenylacetyl chloride 
• 101-97-3 Ethyl 2-phenylethanoate 

Downstream Products

• 58007-81-1 dimethylthiocarbamoylsulfanyl-phenyl-acetic acid 
• 33224-94-1 butoxy-phenyl-acetic acid 
• 96-09-3 styrene oxide 
• 4755-72-0 Chloro-phenyl-acetic acid 
• 1004-99-5 2-chloro-2-phenylethanol 
• 1762-68-1 2-amino-5-phenyl-4-thiazolidinone 
• 101450-09-3 (2-diethylamino-ethoxy)-phenyl-acetic acid ethyl ester 
• 95770-77-7 4-phenyl-hexahydro-pyrido[2,1-c][1,4]oxazin-3-one 
• 95770-79-9 3-phenyl-hexahydro-pyrido[2,1-c][1,4]oxazin-4-one 
• 5595-82-4 2-methylamino-5-phenyl-selenazol-4-one 
• 5533-94-8 2-imino-3-methyl-5-phenyl-selenazolidin-4-one 
• 100026-96-8 1,4-diphenyl-hexahydro-pyrido[2,1-c][1,4]oxazin-3-one 
• 100026-95-7 1,3-diphenyl-hexahydro-pyrido[2,1-c][1,4]oxazin-4-one 
• 90915-12-1 2-imino-3-methyl-5-phenyl-thiazolidin-4-one 

Relevant academic research and scientific papers

Efficient α-chlorination of carbonyl containing compounds under basic conditions using methyl chlorosulfate

An efficient method for the α-chlorination of ketones under basic conditions is described using methyl chlorosulfate. Its applicability for the chlorination of other functional groups has also been studied and it is equally useful for the synthesis of α-chloroesters and amides. Methyl chlorosulfate is described for the first time as a positive chlorine source. Some aldol reactions which occur during the chlorination of some substrates are also reported.

Iodobenzene Dichloride in the Esterification and Amidation of Carboxylic Acids: In-Situ Synthesis of Ph3PCl2

A novel, in-situ synthesis of dichlorotriphenylphosphorane (Ph3PCl2) is accomplished upon combining PPh3and the easily prepared hypervalent iodine reagent iodobenzene dichloride (PhICl2). The phosphorane is selectively generated in the presence of carboxylic acid or alcohol residues to rapidly produce acyl chlorides and alkyl chlorides in high yields. Addition of EtOH, PhOH, BnOH, Et2NH or CH2N2results in the direct synthesis of esters, amides and diazo ketones from carboxylic acids.

SUBSTITUTED PHENYLLUREAS AND PHENYLAMIDES AS VANILLOID RECEPTOR LIGANDS

The invention relates to substituted phenylureas and phenylamides of formula (I), to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions.

Vanilloid receptor ligands, pharmaceutical compositions containing them, process for making them and use thereof for treating pain and other conditions

Compounds corresponding to formula I: which act as vanilloid receptor ligands, pharmaceutical compositions containing such compounds, a process for the producing such compounds, and the use thereof to treat or inhibit pain and/or various other disorders or conditions.

Enzymatic hydrolysis and selective racemisation reactions of α-chloro esters

The kinetic resolution of α-chloro esters was effected with good selectivity using CLEC (Cross-Linked Enzyme Crystals) enzymes. The selective racemisation of α-chloro esters in the presence of α-chloro acids enabled a successful dynamic kinetic resolution reaction to be performed.

Effect of fluorine substitution of α-and β-hydrogen atoms in ethyl phenylacetate and phenylpropionate on their stereoselective hydrolysis by cultured cancer cells

(±)-Ethyl 2-fluoro-2-phenylacetate was stereoselectively hydrolyzed by cultured cells of several rat cancer cell lines to give the carboxylic acid rich in the R enantiomer. The stereoselectivity increased for (±)-ethyl 2-fluoro-2-phenylpropionate (2b) with all present cell lines and for (±)-ethyl 2-phenyl-3,3,3-trifluoropropionate (3b) with rat hepatoma McA-RH7777 cell line. The stereoselectivity was different for the different cell lines, as McA-RH7777 cells preferred (R)-2b in contrast with the preference towards (S)-2b by other cells such as ras oncogene-transformed rat liver Anr4 cells. These stereoselectivities were different from those for non-fluorinated (±)-ethyl 2-phenylpropionate. Thus fluorine atoms are recognized by ester hydrolases of cancer cells, and fluorine substitution on the acyl group will be useful for making ester-type anticancer prodrugs more specific to cancer cells.

Synthesis of 4-oxo-2-azetidineacetic acids by means of radical cyclization of N-vinylic α-bromo amides

Bu2SnH-mediated radical cyclization of α-bromo amide 8, bearing phenyl and phenylthio substituents at the terminus of the N-vinylic bond, proceeded in a 4-exo-trig manner to give β-lactam 9. Ruthenium tetroxide oxidation of the phenyl group incorporated into the product 9 provided a new synthesis of 4-oxo-2-azetidineacetic acid 13, a useful intermediate for (±)-PS-5. Chiral 4-oxo-2-azetidineacetic acids 23 and 36, key intermediates for the synthesis of (+)-PS-5 and (+)-thienamycin, respectively, were also obtained through the asymmetric radical cyclization of N-vinylic α-bromo amides having chiral auxillaries at the side-chain.