Esters of sulfonic acids. VI. Preparation and reactions of alkylisothiourea p-toluenesulfonates was written by Klamann, D.;Drahowzal, F.. And the article was included in Monatshefte fuer Chemie in 1952.Reference of 1843-21-6 This article mentions the following:
ROC8H17 (R = p-MeC6H4SO2) (28.4 g.), refluxed 1 hr. with 7.6 g. thiourea in 80 cc. absolute alc., cooled to -20°, filtered, the mother liquor concentrated, the product crystalline and filtered, and the remaining solution treated with ether, gave a total of 98% practically pure octylpseudothiourea p-toluenesulfonate (I), m. 112-13°. When the alkylpseudothiourea salt (II) is not to be isolated, 96% alc. may be used; the alc. is distilled, and the residue heated to dryness (steam bath). ROMe (46.5 g.) and 19 g. thiourea in 20 cc. water, heated gently with stirring until the mixture was homogeneous, then heated to dryness, gave 99% Me derivative (III), m. 144-5°. The following II were prepared, [% yield of purified product and m.p. (from absolute alc. unless specified), given]: III, 93, 144-5°; Et (IV), 90, 125-6°; Bu, 87, 166°; iso-Bu, 88, 156-7°; hexyl, 87, 139.5-40.5° (from H2O); I, 85, 112.5-13.5° (from (C6H6); dodecyl (1.5-hr. reaction time), 88, 102-3° (from C6H6); octadecyl (1.5-hr. reaction time), 88, 103.4-4.5°; PhCH2, 80, 181.5-2.5°; cyclohexyl, 51, 169° (decomposition); 1,2-ethanedi (V) (0.5-hr. reaction time), 84, 269-79° (decomposition) (from H2O); 1,6-hexanedi (VI), 84, 236-6.5° (from H2O); ClCH2CH2, 34 (40% V.HCl as by-product), m. 141.5-2.5° (reaction time 15 min., 50% yield with 8% V). ROCH2CH2Cl with PhOH gives a trace of (CH2OPh)2, with PhSH 55% (CH2SPh)2. Thiourea and ROPh or the p-NO2 derivative (0.1 mol. each), heated 6 hrs. in 100 cc. absolute alc. gave 97-8% recovery of ROPh. To stirred 38 g. RCl and 26 cc. EtOH was added (30 min., 12-17°) 32 cc. 25% NaOH and the mixture stirred 2 hrs. at 15-18°, neutralized with HCl, treated with 13 g. thiourea and warmed 1 hr. on a water bath, concentrated to dryness, and extracted with absolute alc., giving 83% IV, m. 125-6°. To 0.2 mol. III in 300 cc. H2O, stirred at -2 to 3°, was added Cl, the solution turning green; after 100 min. the liquid product was extracted with ether, washed with 5% NaHSO3 and H2O, dried, concentrated, and distilled giving 75% MeSO2Cl, b9 46-7°, nD20 1.4505, 98.34% pure (Drahowzal and Klamann, C.A. 45, 10134d). Similarly the following sulfonyl chlorides were prepared (solid products were filtered, washed, dried, taken up in ether, filtered, and recrystallized), (% yield, b9, and nD20 or m.p., and purity, resp., given): Et, 87, 55-5.5°, 1.4539, 98.51; Bu, 85, 80-1°, 1.4559, 98.64; hexyl, 85, 106.5-7°, 1.4585, 99.94; dodecyl, 87, m. 42-3°, 98.19; PhCH2, 88, m. 91-2°, 97.23: 1,6-hexanedi, 80, m. 82-3°, 98.80; ClCH2CH2, 75, 81-2°, 1.4925, – (EtSO2Br, 58, 73-4°, -, 95.31; EtSO2NH2, m. 59-60°). VI (23.2 g.) refluxed 2 hrs. with 9 g. KOH in 100 cc. H2O, cooled, diluted with H2O, acidified with dilute H2SO4, extracted with ether, and the extract washed, dried, concentrated, and distilled, gave 5.6 g. HS(CH2)6SH, b12 105.5-6°, nD20 1.5106. Similarly the following mercaptans were prepared: 78% Et, b754 34.5°; 84% Bu, b752 97-8°; 86% octyl, b20 88.5°, nD20 1.4541; and 24% cyclohexyl. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Reference of 1843-21-6).
N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. Thiazoles frequently appear in peptide studies. Thiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Reference of 1843-21-6
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica