Sodium ethanethiolate

Salts are formed as with oxygen-containing compounds. For example, C2H5 — S—Na is named either sodium ethanethiolate or sodium ethyl sulfide. If mercapto- has been used as a prefix, the salt is named by use of the prefix sulfido- for —S . 

Sodium ethanethiolate has been examined for the selective cleavage of aryl methyl ethers. Methyl ethers para to an electron-withdrawing group are cleaved preferentially. ... 

Only a few exchange reactions of substituents directly bound to the heterocyclic ring have been reported. Gompper has studied the nucleophilic substitution of bromo- and chloro-l,2,3-triazines and observed replacement of bromine or chlorine with sodium ethoxide, sodium ethanethiolate and amines. In most cases yields are quantitative. With the trihalo compound, first the 4-mono- then the 4,6-di-substituted derivative is obtained (79CB1529). Reaction of 5-chloro-2-methyl-4,6-bis(dimethylamino)-l,2,3-triazinium iodide (61) with malononitrile affords compound (62). Compounds of the general structure (63) are hydrolyzed to l,2,3-triazin-5(2//)-ones (64) (79CB1535). 

The problem states that the reaction is first order in (CH3)3CC1 (tert-butyl chloride) and first order in NaSCH2CH3 (sodium ethanethiolate). It therefore exhibits the kinetic behavior (overall second order) of a reaction that proceeds by the E2 mechanism. The base that abstracts the proton from carbon is the anion CH3CH2S . 

Reaction of styrene oxide with sodium ethanethiolate completes the synthesis. 

With activated manganese dioxide as the oxidizing agent, the yield was only 1 %. Attempted oxidations with silver carbonate, chromium trioxide, and lead tetraacetate were unsuccessful1. 2-(Methoxyphenyl)tellurophenes were converted to 2-(hydroxyphenyl)tellurophenes upon treatment with sodium ethanethiolate or boron tribromide2. 

A mixture consisting of 3-bromo-6-methoxy-2-(4-methoxyphenyl)-lH-inden-l-one (0.4345 mmol), sodium ethanethiolate (1.09 mmol) and 0.5 ml triethylamine dissolved in 3 ml DMF was heated 24 hours at 80°C and then cooled. The mixture was then poured into water and extracted with EtOAc. Extracts were washed with brine, dried, purified by flash chromatography using 10% EtOAc/petroleum ether, and the product isolated in 89% yield as a dark red solid, mp = 88-90°C. 

During a synthesis of quinone imine precursors to the Dynemicins, Myers and co-workers100 encountered problems with the lability of the dimethyl acetal function in 56,1 [Scheme 1.56] whilst removing the robust phenolic methyl group using sodium ethanethiolate in hot DMF, However prior conversion of the free hydroxy function in the substrate to the magnesium salt 56.2 by reaction with ethylmagnesium bromide afforded protection for the dimethylacetal under the strenuous conditions of nucleophilic demethylation. 

O- and Se-Demethylation. Sodium methaneselenolate cleaves methyl aryl ethers and sulfides. HMPT is preferred to DMF as solvent. Sodium ethanethiolate cleaves various alkyl aryl selenides in refluxing HMPT or DMP... 

Addition of sodium ethanethiolate to 3-chloro-4,4,4-trifluoro-2-phenylbut-2-cnal (23) furnishes the substituted but-2-enal derivative 24 in good yield. 

Hydroxyphenyl)-telliirophene 0.92 g (11 mmol) of sodium ethanethiolate are dissolved in 9 ml of dimethylformamide (DMF), the solution is stirred under nitrogen, and 0.4 g (1.4 mmol) of 2-(4 -meth-ox) phenyl)-tellurophene in 9 ml of DMF are added. The mixture is heated at 80° for 144 h, cooled, diluted with water, and extracted with diethyl ether. The aqueous phase is acidified with 10% hydrochloric acid, the acidified aqueous phase is extracted with diethyl ether, and the organic extracts are combined, dried with anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue is chromatographed on silica gel with light petroleum ether (b.p. 40-60°)/diethyl ether (4/1, v/v) as the mobile phase. The product is recrystaUized from ligroin/chloroform (1/1, v/v) yield 0.1 g (26%) m.p. 160 . 

Hirata, M, Studies on nucleosides and nucleotides. IX. Nucleophihc substitution of secondary suEonyloxy groups of pyrimidine nucleosides. II. Reaction of 2,2 -anhydro-l-(3 -0-tosyI-p-D-arabinofuranosyI)uraciI with sodium bromide, sodium ethanethiol and sodium azide, Chem. Pharm. Bull, 16, 291-295, 1968. 

Due to the high nucleophilicity of the thiolate anion, exchange of halogen substituents meets with no difficulties. Both chloro substituents in 2,4-dich1oropyrido[2,3-d]pyrimidine (21) are replaced by ethylsulfanyl groups by refluxing with sodium ethanethiolate in ethancthiol.77... 

Alkylthio derivatives are normally prepared by alkylation of thiones, but they can also be prepared by alkanethiolysis reactions. Aromatic sulfides are commonly prepared by arenethiolysis in reactions with halopyrimidines . Selective thiolysis can be effected, as exemplified by the preparation of 2-chloro-4-ethylthio-5-fluoropyrimidine from 2,4-dichloro-5-fluoropyrimidine by sodium ethanethiolate (72%) <69ACS294>. 

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