20568-14-3

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• 25445-77-6 4-phenyl-1,2,3-thiadiazole 
• 75-08-1 ethanethiol 
• 83893-97-4 (thiocyanatoethynyl)benzene 
• 298-06-6 O,O-Diethyl hydrogen phosphorodithioate 
• 103-80-0 phenylacetyl chloride 
• 103-82-2 phenylacetic acid 

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• 5873-91-6 phenyldithioacetic acid 
• 21017-70-9 N-Cyan-thiolimido-phenylessigsaeure-methylester 
• 142133-83-3 2,3-Diphenyltetrathiobernsteinsaeure-diethylester 
• 20761-86-8 2-Phenyl-dithiopenten-⁽⁴⁾-saeureaethylester 
• 23296-81-3 N,N'-Dicyan-phenylacetamidin-kalium 

Relevant academic research and scientific papers

THE REACTION OF CARBOXYLIC ACID CHLORIDES WITH O,O-DIALKYLDITHIOPHOSPHORIC ACIDS

At high temperature (130 deg C), carboxylic acid chlorides react with O,O-dialkyldithiophosphoric acids (RO)2P(=S)(SH), Ia-c to give the corresponding dithiester RC(=S)(SR) II in varying yields, while benzoyl chloride reacts with compounds Ia, b at 20 deg C to give the corresponding S-benzoyl-O,O-dialkyldithiophosphate (RO)2P(=S) IIIa, b.Mechanistic consideration on the formation of the products are discussed.Key words: Carboxylic acid chlorides; O,O-dialkyldithiophosphoric acids, and S-benzoyl-O,O-dialkyldithiophosphates.

STUDIES ON ORGANOPHOSPHORUS COMPOUNDS XLVIII Synthesis of Dithioesters from P,S-Containing Reagents and Carboxylic Acids and Their Derivatives

2,4-Bismethylthio-1,3,2,4-dithiadiphosphetane 2,4-disulfide, IIa, is prepared from O,O-dimethyldithiophosphoric acid, Ia, and P4S10 at 160 deg C. 2,4-Bis(4-phenoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide, IIc, and 2,4-bis(4-phenyl-thiolphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide, IId, are prepared at 160 deg C from P4S10 and diphenylether and diphenylsulfides, respectively.Carboxylic acids RCOOH (R=CH3, C2H5, n-C3H7, n-C4H9, C6H5CH2, C6H5) react with compound Ia at 130 deg C to give the corresponding methyl dithioesters.Carboxylic acids RCOOH (R=C6H5-CH2, C6H5) react with compound Ib at 200 deg C for 15 min to give the corresponding ethyl dithioesters, while low boiling acids (R=CH3, C2H5, n-C3H7) yielded mixtures of the corresponding ethyl dithioester and ethyl carboxylate.Carboxylic acid chlorides RCOCl (R=ClCH2, C2H5, t-C4H9, C6H5CH2, C6H5, p-NO2C6H4) react with compound IIa at 80 deg C to give the corresponding methyl dithioesters in good yields.S-Substituted thioesters react with IIc at 85 deg C to give the corresponding dithioesters in good yields.Dihydro-2(3H)-furanone, VI, and 5-methyl-2(3H)-furanone, VII, react with IIa at 80 deg C to give dihydro-2(3H)-thiophenethione, VIII and 2,2'-dithiobis(5-methyl thiophene), IX, respectively.Also XI reacts with IIa, IIc, and IId to give VIII in nearly quantitative yields.

Reactions of 1-alkynyl thiocyanates with nucleophilic reagents. Synthesis of 2,4-disubstituted 1,3-thiazoles

Reaction of 1-alkynyl thiocyanates RCC-S-CN (1) with alcohols, phenol or thiols or secondary aliphatic amines in the presence of anhydrous zinc chloride or boron trifluoride diethyl etherate gives mixtures of 2,4-disubstituted 1,3-thiazoles (2), thiocarbonyl compounds (3) (thiono esters, dithio esters or thioamides) and 2-alkylidene-1,3-dithioles (4).In all cases, the 1,3-thiazoles can be obtained in good yields if the proper reaction conditions are applied.Interaction between 1 and lithium dialkylamides LiNR'2 gives the compounds RCC-S-NR'2 (5) (attack on sulfur).With alkoxides R'O1-, the primary attack is on CN: the in termediacy alkynethiolate RCC-S1- subsequently reacts with the alkyl cyanate R'OCN to afford 1-alkynyl sulfides RCC-SR'(6)