Synthesis of Unsymmetrical Bis(imidoyl)dichlorides of Oxalic Acid

Helmholz, Falko; Schroeder, Rita; Langer, Peter

doi:10.1515/znb-2005-1112

Cited by 4 publications

(1 citation statement)

References 2 publications

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“…To a stirred mixture of primary amine (1 mmol), CS 2 (1 mmol) and Et 3 N (2 mmol) was added a solution of N,N'-diphenyloxalimidoyl dichloride [22,23] (1 mmol) in DMF (3 mL) at room temperature. After completion of the reaction [about 8 h; TLC (AcOEt/hexane 1:5) monitoring], the mixture was diluted with AcOEt and aq NH 4 Cl (3 mL) and stirred for 10 min.…”

Section: General Proceduresmentioning

confidence: 99%

A one-pot synthesis of functionalized 4,5-bis(phenylimino)-1,3-thiazolidine-2-thiones from primary amines, CS2 and N,N’-diphenyloxalimidoyl dichloride

2016

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activities [1], while others have found application as liquid crystals [6] and cosmetic sunscreens [7].Recently, new methods for the synthesis of 1,3-thiazole derivatives have been reported [8][9][10][11][12]. 1,3-Thiazolidine-2-thione derivatives contain a carbamodithioate moiety and have received considerable attention due to their numerous biological activities and their pivotal role in agriculture and as linkers in solid-phase organic synthesis [13][14][15]. The reaction of dianionic compounds with oxaldiimidoyl dichlorides has been reviewed [16]. Therefore, synthesis of these compounds received considerable attention. Previously, several examples of the reaction between dithiocarbamates with nitrogen-containing derivates of oxalic acid have been reported [17].As part of our current studies on the synthesis of sulfurcontaining organic compounds [18][19][20][21], we describe an efficient one-pot method for the direct synthesis of functionalized cyclic carbamodithioate from the reaction of primary amines (1) and CS 2 in the presence of N,N'-diphenyloxalimidoyl dichloride (3) at room temperature. ExperimentalPrimary amine, CS 2 , solvents were obtained from Merck and used without further purification. N,N'-diphenyloxalimidoyl dichloride (3) was synthesized according to the reported procedure. M.p.: Electrothermal-9100 apparatus. IR spectra: Shimadzu IR-460 spectrometer; band positions in cm −1 . 1 H and 13 C NMR spectra: Bruker DRX-300 Avance instrument at 300 and 75 MHz, respectively; δ in ppm, J in Hz. MS: Finnigan-MAT-8430EI-MS mass spectrometer; at 70 eV; in m/z (rel. %). Elemental analyses: Vario EL III CHNOS elemental analyzer.Abstract A simple one-pot synthesis of functionalized 4,5-bis(phenylimino)-1,3-thiazolidine-2-thione derivatives through the reaction of primary amines and carbon disulfide in the presence of N,N'-diphenyloxalimidoyl dichloride at room temperature is described. Graphical AbstractCS 2 + NPh PhN Cl Cl + Et 3 N (2 eq) DMF, r.t.; 8 h RN S PhN NPh S R-NH 2

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Section: General Proceduresmentioning

confidence: 99%