58863-41-5

Upstream product

• 100-14-1 4-nitrobenzyl chloride 
• 74-88-4 methyl iodide 
• 82737-61-9 2,4-bis(methylthio)-1,3-dithia-2,4-diphosphetane-2,4-disulfide 
• 122-04-3 4-nitro-benzoyl chloride 
• 99-99-0 1-methyl-4-nitrobenzene 
• 74-93-1 methylthiol 
• 7291-01-2 N,N-dimethyl-4-nitrobenzamide 

Downstream Products

• 42754-63-2 3-amino-5-(4-nitro-phenyl)-1⁽²⁾H-pyrazole-4-carbonitrile 
• 183738-68-3 3-(4-tert-butoxycarbonylamino-phenyl)-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine 
• 183739-67-5 3-(4-nitrophenyl)-3-methylmercapto-2-cyano-acrylonitrile 
• 95016-10-7 4-Nitro-thiobenzoic acid hydrazide 

Relevant academic research and scientific papers

THIOLATION WITH DIALKOXY DISULFANES - A NEW METHOD FOR THE PREPARATION OF DITHIOESTERS

CH-acidic methyl groups can easily be converted into dithioesters by use of sulfur transfer reagents possessing a S2-unit and two leaving groups.A possible mechanism is discussed.

Dithiocarboxylic Acids, Dithiocarboxylic Esters, or Thiocarboxylic Amides by Reaction of Methylene-active Chloromethyl Compounds with Sulfur

With a mixture of sulfur and amine in DMF at room temperature halomethyl compounds (1,5-10) can be oxidized to give thiocarboxylic acids (2,11-16) and their derivatives (3,4,17-35).We studied this reaction in detail especially with chloroacetic derivatives (11-15) or chloromethyl heterocycles (16) formally derived from chloroacetic acid.The resulting thiooxalic acid derivatives (11-27) represent activated acids and very useful C2-synthons, especially for the synthesis of heterocycles.Oxidation in the presence of triethylamine leads to dithiocarboxylates (11-16) which can be alkylated to dithioesters (17-27) in high yields.As a rule, with different primary and secondary amines instead of tertiary amines these dithiocarboxylates or dithiocarboxylic esters can be transformed already at low temperatures to thioamides (28-35).

ELEKTROCHEMISCHE OXIDATION VON DITHIOCARBONSAEUREESTERN ZU ISOTHIAZOLEN

Electrolysis of alkyl arenedithioates 1 in acetonitrile with benzyl-triethyl-ammonium chloride as supporting electrolyte yields 5-aryl-4-cyano-3-methyl-isothiazoles 4.A reaction path is discussed according to which the dithioesters 1 are chlorinated at the anode and subsequently react with 3-iminobutyronitrile (6), generated at the cathode, to form the isothiazoles 4.

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.