Su, Helen C. F. published the artcileSynthesis of possible cancer chemotherapeutic compounds based on enzyme approach. III. 1,2,3-Oxadithiolane 2-oxide, Product Details of C4H8Cl2S2, the publication is Journal of Organic Chemistry (1961), 4993-5, database is CAplus.
1,2,3-Oxadithiolane 2-oxide (I) was prepared from mercaptoethanol (II) and SOCl2 in CHCl3. The 5-Me derivative (III) was prepared by this method. Attempted preparation of the 5-Ph derivative under the same conditions led only to 2,5-diphenyl-p-dithiane (IV). Treatment of I with K2CO3 gave CO2, SO2, and ethylene sulfide. Bromination of I with Br yielded bis(2-bromoethyl) disulfide (V) and with N-bromosuccinimide, yielded N-(2-bromoethylthio)succinimide (VI). II (156 g.) in 150 ml. CHCl3 and 262 g. SOCl2 added dropwise into 200 ml. CHCl3 at room temperature and stirred 5 hrs. gave 176 g. I, b3 77-9°, n20D 1.5771, 22.3% 2-chloro-2′-mercaptodiethyl sulfide, b4 91-4°, n20D 1.5653, 1.5% p-dithiane, flakes, m. 111-12°, and a residual paste which, treated with hot concentrated H2SO4-HNO3, gave a gray sponge. Isopropenyl acetate (20 g.) treated dropwise with 16.7 g. thiolacetic acid and the mixture heated 2 hrs. gave 74% 1-acetoxythioisopropyl acetate (VII), b0.65-0.70 56.5-8.0°, n33D 1.4635. VII refluxed with 1% MeOH-HCl for 7 hrs. and evaporated gave 2-hydroxypropyl mercaptan, b46-7 75-9°, n30D 1.4818. III, prepared in 3 hrs. at 28-30° by the same method used for I, b1.7-2.1 72-85°, m. 39-9.5°; distillation of the residue gave a dark liquid, b1.6-2.1 82-120°. Attempted redistillation of this product led to severe decomposition Styrene oxide (36 g.) added in 5 hrs. to 30 g. Ba(OH)2 in 75% alc. saturated with H2S below 30°, H2S passed in for 1 hr. longer and the mixture saturated with CO2 and extracted gave 76.8% 1-phenyl-2-mercaptoethanol (VIII), b3.7-4.1 124.5-7.0°, n27D 1.5803. VIII (31.5 g.) and 35.7 g. SOCl2 added simultaneously to CHCl3 at 25-30°, stirred 5 hrs., evaporated, and the liquid treated with C in CHCl3, concentrated, and triturated with Et2O gave IV, flakes, m. 212-14°. The solvent filtrate further concentrated gave rhombic crystals of S, m. 113-15°. Equimolar amounts of I and K2CO3 heated to the point where gas was evolved gave almost quant. yields of CO2 and SO2 and 2.3 ml. ethylene sulfide, b. 55-6°, n20D 1.4821. I (12.4 g.) was added dropwise to a preheated flask at 270°/130-5 mm. and the products distilled to give S and unchanged I, H2O and a rubbery substance, and a mixture of SO2, H2O, and more rubbery product. I (12.4 g.) in 100 ml. CCl4 treated at -5° with 16 g. Br in 20 ml. CCl4, and the mixture stirred 5 hrs. at room temperature and distilled gave 4.5 g. V, b0.5-.055 103-6°, n19D 1.6190. N-Bromosuccinimide (17.8 g.) added portionwise to 12.4 g. I in 100 ml. CCl4 at 15-20° and the mixture heated 6 hrs. at 25-30° gave 8 g. VI, m. 89-90.5°. The liquid was evaporated to give a small amount of V. I (28.3 g.) containing 0.1 g. Bz2O2 treated at -5° with Cl, stirred 3 hrs. at 0°, then overnight at room temperature, and distilled gave 63% V. I (12.4 g.) and 13.4 g. N-chlorosuccinimide refluxed 8 hrs. in 100 ml. CCl4 gave succinimide. The CCl4 solution afforded some I and 1.5 g. bis(2-chloroethyl) disulfide, b0.8 80-7°, n20D 1.5634. III treated with Br in CCl4 as above gave bis(g-bromopropyl) disulfide, b0.8 113-14°, n22D 1.5805. Infrared spectra were given for the above compounds
Journal of Organic Chemistry published new progress about 1002-41-1. 1002-41-1 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is 1,2-Bis(2-chloroethyl)disulfane, and the molecular formula is C8H5F3O2S, Product Details of C4H8Cl2S2.
Referemce:
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