ethylene thiolcarbonate

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Properties of substance:

1,3-oxathiolan-2-one

Synonyms:

ethylene thiolcarbonate

Group of substances:

organic

Empirical formula (Hill's system for organic substances):

C₃H₄O₂S

CAS №: 3326-89-4

Synthesis 1:

Reference: Jones F. N., Andreades S. Ethylene thionocarbonate and 1,3-oxathiolane-2-thione / Journal of Organic Chemistry. - 1969. - Vol. 34, No. 10 pp. 3013 [doi: 10.1021/jo01262a047]

A mixture of 0.52 g (5 mmol) of 1,3-dioxolane-2-thione, 3 g of KI, and 20 ml of acetonitrile was stirred and heated at 60° for 68 hr. Removal of solvent and salts gave 0.4 g of essentially pure ethylene thiolcarbonate, identical with a sample prepared by Reynolds.

Synthesis 2:

Reference: Reynolds, D. D. A New Method for the Preparation of Ethylene Sulfide / Journal of the American Chemical Society. - 1957. - Vol. 79, No. 18 pp. 4952 [doi: 10.1021/ja01575a033]

Two hundred and thirty-seven grams of pyridine and one hundred grams of ethyl acetate were stirred together at 10°. A solution of 150 g. of phosgene in 300 ml. of ethyl acetate was cooled to -15° and 158 g. of 2-mercaptoethanol was added to it. This cold solution was added gradually to the stirred pyridine solution. The reaction temperature was maintained at 15—20°. After all the phosgene had been added, the reaction mixture was stirred for an additional 30 minutes at 35°, after which it was washed by stirring rapidly in an equal volume of cold water containing 10 ml. of concentrated hydrochloric acid. The ethyl acetate layer was washed with an equal volume of cold water, dried over anhydrous magnesium sulfate, and then ethyl acetate was removed by distillation under reduced pressure. The oily residue was then distilled through a 10-in. Vigreux column equipped with a variable-reflux take-off head; yield, 80 g., b.p. 50—60° at 1.0—1.5 mm., n(25, D) 1.5104; residue of polymer 47 g. Redistillation of the monothiolethylene carbonate gave 75 g. (48.1%), b.p. 47—50° at 0.08 mm., n(25, D) 1.5104. Analysis indicated the polymer is (-CH2-CH2-S-CO-O)4.

Anal. Calcd. for C3H4SO2: C, 34.6; H, 3.8; S, 30.7. Found: C, 34.6; H, 3.9; S, 31.1. Found for the polymeric residue: C, 34.4; H, 4.2; S, 30.1; mol. wt., 415.

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