1,3-oxathiolane-2-thione

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Properties of substance:

1,3-oxathiolane-2-thione

Group of substances:

organic

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

C₃H₄OS₂

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 1-l. 3-necked flask containing 172 g (0.50 mol) of ((2-hydroxyethyl)thio)lead(II) acetate and 600 ml of methylene chloride was surrounded by a large bath of water at about 15°. The slurry was stirred as 35 ml (52 g, 0.45 mol) of thiophosgene was added by means of pipets. The mixture was stirred for 20 hr with minimum exposure to light. During the first 5 hr, the temperature was maintained at 18—25° by occasional addition of ice to the water bath to keep it at 10—15°. Later, the bath and the reaction flask were allowed to warm to ambient temperature. The mixture was filtered. The liquid was concentrated on a rotary evaporator, keeping the temperature below 25°, to give 55 g of pale yellow oil. The oil was chromatographed on a 9.5-cm column of 1 kg of neutral silica gel (Woelm activity I) using methylene chloride to elute the product. Most by-products, including substantial amounts of (HOCH2CH2S)2CS, were not eluted. The yellow-orange eluent was collected in fractions. Concentration of the earlier fractions gave 25 g (46%) of 1,3-oxathiolane-2-thione, containing a few per cent 1,3-dithiolan-2-one. Distillation with a high-vacuum Vigreux apparatus gave 18 g of pale yellow liquid, bp 56—62° (0.08—0.1 μ). All fractions contained about 5% 1,3-dithiolan-2-one. The product should be stored under cold, dry, dark conditions. Further purification by zone refining did not remove the side isomer.

Anal. Calcd for C3H4OS2: C, 29.98; H, 3.35; S, 53.35. Found: C, 30.00; H, 3.50; S, 53.44.

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