5-ethylthio

Methylthio- and 2-ethylthio-4-methylthiazoles undergo reductive ring opening when treated by sodium in liquid ammonia (204). The first step of this reaction consists of the formation of the A-4-thiazoline anion (80). The next steps are analogous to those given for 80a to 83. 

IR spectra of 2-substituted 1-azetines show the expected trends in the frequency of the imine absorption thus 2-aryl-l-azetines generally show vq=n at ca. 1550-1580 cm while 2-ethylthio and 2-alkoxy-1-azetines show absorptions at ca. 1535 and 1620 cm respectively (79CB3914, 67JHC619, 69LA(725)124). The parent 1-azetine shows vc=n at 1570 cm ... 

O-Alkylation of the readily available iV-unsubstituted azetidin-2-ones (/3-lactams) constitutes a versatile route to 2-alkoxy-l-azetines (cf. Section 5.09.3.2.3). Thus treatment of the /3-lactams (266) with trialkyloxonium tetrafluoroborates followed by basification affords the 2-alkoxy-l-azetines (267) in moderate yields (67JHC619,69LA(725)124). Similar treatment of the azetidine-2-thiones (268) (available from thiation of the corresponding /3-lactams with phosphorus pentasulfide) affords the analogous 2-ethylthio-1-azetines (269) (67JHC619), which are generally more stable than their 2-alkoxy analogues. 

The Diels-Alder reaction catalyzed by this chiral titanium catalyst 31 has wide generality (Scheme 1.53, 1.54, Table 1.22, 1.23). Acryloyl- and fumaroyl-oxazolidinones react with isoprene giving cycloadducts in high optical purity. 2-Ethylthio-l,3-buta-diene can also be successfully employed as the diene [42]. 

Thiazoline, 2-ethylthio [Thiazole, 2-(ethylthio)-4,5-dihydro-], 82 2 Thiazohne, 2-mercapto [2 Thiazohdine-thione], 77... 

Ethylthio)ethanol, el80 Ethyl thioglycolate, el96... 

Dipolar cycloadditions of 2-ethoxy- and 2-ethylthio-l-azetines 146 (Z = O, S) with nitrile oxides give 4,5,6,6a-tetrahydroazeto[l,2-d]oxadiazoles, for example 147 (315, 316). 

Chemical name 0, 0-Diethyl S-[2-(ethylthio)ethyl]-phosphorodithioate Worthing 1987... 

Brodeur J, DuBois KP. 1964. Studies on the mechanism of acquired tolerance by 0,0-diethyl S-2 (ethylthio) phosphorodithioate (Di-Syston). Arch Int Pharmacodyn Ther 149 560-570. 

Fawade MM, Pawar SS. 1978. Alterations in mixed function oxidase system during thiodemeton (o-o diethyl S-2(ethylthio) ethyl phosphorothioate) toxicity. Indian J Exp Biol 16 481-484. 

Kleinschmidt MG Jr. 1971. Fate of Di-Syston 0,0-diethyl S-2-(ethylthio) ethyl phosphorodithioate in potatoes during processing. J Agric Food Chem 19 1196-1197. 

Ibrahim, F.B., Gilbert, J.M., Evans, R.T., and Cavagnol, J.C. Decomposition of disyston (0,0-diethyl 5-[2-(ethylthio)ethyl] phosphorodithioate) on fertilizers by infrared, gas-liquid chromatography, and thin-layer chromatography. J. Agric. Food Chem., 17(2) 300-305, 1969. 

Ethyl 2-ethylthio-4-chloro-5-pyrimidinecarboxylate (XXIIa), as well as the corresponding4-hydroxy-(XXIIb) and 4-amino-(XXIIIa) derivatives, possess-anti-cytogenic activity on Neurospora crassa [223, 224]. Compounds (XXIIIa, b and c) were found to inhibit the conversion of orotic acid to the uridine nucleotides [202]. Ethyl 2-methylthio-4-(halo-substituted anilino)-5-pyrimidinecarboxylates (XXIV), particularly the o-bromo- and the o-chloro- derivatives, substantially inhibit the growth of five experimental mouse tumours (Krebs-2 ascites carcinoma, Ehrlich carcinoma clone 2, leukaemia L-1210, carcinoma 755 and lymphocytic neoplasm P-288) [225]. Compounds of this type are usually prepared by the base catalysed condensation of ethoxymethylenemalonic esters or related derivatives with urea, thiourea, guanidine, or substituted amidine-type analogues [212, 225-237]. 

Synonyms Mixture of 0,0-diethyl S-(and 0)-2-[(ethylthio)ethyl] phosphorothioates Mer-captofos Demox Systox... 

Deprotonation of the monosulfoxide (Z)-l-(ethylsulfinyl)-2-(ethylthio)ethene, obtained from 1,2-dimercaptoethene, with terf-butylhthium in THF followed by quenching with deuterium oxide showed complete monodeprotonation at the vinylic position33. 

The stronger inductive effect of the sulfoxide group results in preferential a-deprotonation of (Z)-l-(ethylsulfmyl)-2-(ethylthio)ethene which leads to 1-substituted -products 6 via lithiated intermediate 2. Additionally small amounts of 2-substituted products 7 are formed via intermediate 3 due to /1-dcprotonation. Temperature dependent experiments demonstrate that a-lithi-ated Z-intermediate 2 is configurationally labile and is in equilibrium with the corresponding -intermediate which leads to products 5. 

Zur Herstellung von l-(2-Ethylthio-4-phenyl-l,3-thiazol-2-yl)-4-phenyl-imidazol aus 4(5)-Phe-nyl-imidazol mit 2-Ethylthio-4-phenyl-l,3-dithiolium-perchlorat s. Bd. E4, S.713. 

Durch thermische Umlagerung von 3-(Ethylthio-carbonyl)-2-oxo-5-phenyl-2,3-dihydro-l,3,4-oxadiazol laBt sich 2-Ethylthio-5-phenyl-1,3,4-oxadiazol (45% Schmp. 39-40°) neben 5-Phenyl-2-thiono-2,3-dihydro- und 3-Ethyl-5-phenyl-2-thiono-2,3-dihydro-1,3,4-oxadiazol iso-lieren550. 

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