Chloroethyl Methyl Sulfide

In a i-l. three-necked flask are mixed 150 g. (r.63 moles) of /3-hydroxyethyl methyl sulfide (p. 54) (Note i) and 200 g. of dry chloroform (Note 2). The flask is placed on a steam bath and is fitted with a dropping funnel, a mechanical stirrer, and a condenser. The condenser is fitted with a trap to remove the vapors of hydrogen chloride and sulfur dioxide (page 2). A solution of 204 g. (1.7 moles) (Note 3) of thionyl chloride in 200 g. (135 cc.) of dry chloroform is added dropwise to the /3-hydroxyethyl methyl sulfide over a period of about two hours (Note 4). The reaction mixture is stirred vigorously during this addition and for about four hours after the addition is complete. The chloroform is distilled on the steam bath and the residue is distilled under reduced pressure. The yield is 135-153 g- (75 5 per cent of the theoretical amount) of a product boiling at 55-s6°/3o mm- (Note 5). 

Quantities of material seven times as large as the above may be used without decreasing the yield of the product. 

The chloroform is dried by distillation, and the fraction boiling at 60-61° is used. 

The reaction mixture is heated once when about half the thionyl chloride has been added in order to keep the chloroform refluxing gently. Heating after the complete addition of the thionyl chloride is undesirable. 

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B. Ethyl i-Methylthiol-3-phthalimidopropane-3,3-dicarboxylate. —A mixture of 85 g. (0.26 mole) of ethyl sodium phthalimidomalonate and 43 g. (0.39 mole) of /3-chloroethyl methyl sulfide (p. 18) is heated in an oil bath at 160-165° i11 a i-l- three-necked flask, fitted with a condenser, a thermometer, and a stoppered... 

Chloroethyl methyl sulfide is a vesicant and must be handled with care. It boils at 140 0 under atmospheric pressure. 

The photocatalytic reactions in acetonitrile were observed to have fewer primary products and a higher chemical yield of the desired sulfoxide (Fox et al., 1990). The photocatalytic oxidation of 2-chloroethyl methyl sulfide was found to be faster than the degradation of 2-chloroethyl ethyl. UV/ Ti02, in the presence of oxygen, yields the greatest amount of removal for the alkyl halides. The rate of alkyl halide removal was found to increase with increased concentrations of TiOz. 

Chloroethyl(dimethyl)sulfonium iodide, ClCH2CH,S(CH,)2l (1). The salt, m.p. BBSS , is prepared by reaction of 2-chloroethyl methyl sulfide with CH,I. ... 

The oxidative properties of lipoic acid (see p. 51) also depend on the ease of interconversion of thiol and disulfide bonds. Methionine (34) is one of the eight essential amino acids for human nutrition and is deficient in the diet of vegans luckily, this amino acid can be synthesised for use as a nutritive food additive. One synthetic route uses 2-chloroethyl methyl sulfide (36) and phthalimide (37), as shown in Scheme 24. 

King, J.R. and Monteiro-Riviere, N.A., 1990, Cutaneous toxicity of 2-chloroethyl methyl sulfide in isolated perfused porcine skin, Toxicol. Appl. Pharmacol., 104 167-179. 

Reaction between NaFe(CO) C H (4) and 2-chloroethyl methyl sulfide in tetrahydrofuran solution at room temperature yields a rather unstable orange liquid indicated by analysis and other properties to be CH SCH2CH2Fe(CO)2CgHg. Ultraviolet irradiation of this material in benzene solution gives a complex mixture from which the following compounds can be isolated by chromatography on alumina in benzene solution followed by crystallization from pentane or ethanol of the fractions thus obtained ... 

Obtained by treatment of 2,4-dihydroxy-3-methyl-acetophenone with 2-chloroethyl methyl sulfide in the presence of KOH/BC COj mixture in boiling 2-butanone [4274]. 

Chloroethyl Methyl 1-Chloroacetamide 2-Chloroethyl Vinylsulfide 2-Chloroethyl Vinylsulfone 2-Chloroethyl Vinylsulfoxide 2-Chloroethylchloromethyl Sulfide [(2-Chloroethyl)sulfonyl]ethene 2-Chloroethylthio Ethene 2-(Chloromethyl)-l-propene 2-Chloro-/V-(2-chloroethyl)-N-methylacetamide 2-Ch loro-/V,/V-dimethy lam inoethane 2-Chloro-N,N-dimethylethanamine 2-Chloro-N,N-d imethylethylamine... 

The decontamination efficacy of radioprotective agent aminoethylisothiourea and cystamine on rat skin against SM was comparable to standard decontaminants, such as alco-holate, clay, and Fuller s earth (Knezevic and Tadic, 1996). A mixture containing bovine hemoglobin, gelatin, and poi (a Hawaiian foodstuff) on the hydrolytic kinetics of the mustard simulants, 2-chloroethyl ethyl sulfide, 2-chloro-ethyl methyl sulfide and 2-bromoethyl phenyl sulfide, is reported. The kinetic mechanisms and rate constants were dependent upon the mixtures concentration and viscosity (Cemy and Cemy, 1997). 

Related Reagents. Benzyl Chloromethyl Sulfide r-Butyl Chloromethyl Ether 2-Chloroethyl Chloromethyl Ether Chloromethyl Methyl Ether Chloromethyl Methyl Sulfide (p-Methoxy-benzyloxy)methyl Chloride 2-Methoxyethoxymethyl Chloride 2-(Trimethylsilyl)ethoxymethyl Chloride. 

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