《1,2,4-Thiadiazoles. IX. Synthesis and reactions of 3-alkylthio-5-chloro-1,2,4-thiadiazoles》 was published in Chemische Berichte in 1957. These research results belong to Goerdeler, Joachim; Sperling, Gerhard. Related Products of 38362-15-1 The article mentions the following:
cf. C.A. 51, 12077d. In general, 0.5 mole RSC(:NH)NH2.HBr (I) in 300 cc. H2O, 0.5 mole CCl3SCl (II), and about 0.5 g. emulsifier treated dropwise (3-5 hrs.) at 0° and with vigorous stirring with 80 g. NaOH in 320 cc. H2O, the excess II decomposed with 20-30 cc. 25% NH4OH, and the mixture neutralized and steam-distilled gave RSC:N.S.CCl:N (III) as the lower layer of the distillate, sufficiently pure for further reactions, or it could be purified by distillation in vacuo, R, % yield, b.p./mm., d18, and n21D of the III: Me, 50-5, 98°/17 (m. 29-30°), -, -; Et, 65-70, 115°/13, 1.3861, 1.58285; Pr, 45-50, 131°/18, 1.3177, 1.56865; Bu, 37, 140°/14, 1.2650, 1.55805; tert-Bu, 58, 118°/14, 1.2560, 1.55635; iso-C5H11, 36, 148°/14, 1.2233, 1.54785; PhCH2 (IV), 45-50, 120°/0.2 (m. 49-50°), -, -. The preparation of IV was modified by adding 20-30 cc. ether at first, stirring longer after neutralization, and extracting with ether instead of steam-distilling III treated with a concentrated solution of MeNH2 in MeOH, the resulting MeNH2.HCl and most of the solvent removed, and H2O added gave RSC:N.S.C(NHMe):N (R, m.p., and m.p. of picrate given): Me, 144.5-5.0°, 164.5°; Et, 101-2°, 145°; Pr, 75-6°, 128°; Bu, 89-90°, 123°; tert-Bu, 119-20°, 138°; iso-C5H11, 82-3°, 126.5°; PhCH2, 139-40°, 141.5°. Similarly, with PhCH2NH2 in place of MeNH2, the solvent not removed, and dilute HCl added in place of H2O (to keep the excess PhCH2NH2 in solution) were formed RSC:N.S.C(NHCH2Ph):N (R and m.p. given): Me, 114.5-15.5°; Et, 101-1.5°; tert-Bu, 149.5-50°. Other reagents in very similar reactions with III gave RSC:N.S.CR’:N (V) (reagent used, R, R’, % yield, and m.p. given): PhNH2, tert-Bu, NHPh, 60-5, 146-7.5°; Me2NH, Me, NMe2, -, – (picrate, m. 70.5-1.0°); Me3N, Me, NMe3.HCl, 100, 105° (decomposition) (picrate, m. 128.5-30.0°); N2H4.H2O, Et, NHNH2, 100, 112-14° (decomposition) (the product with BzH and AcONa, R’ = NHN:CHPh, m. 208°); H2S with (NH4)2CO3, Me, HS, 55 g. from 74 g. III, 150-1° (decomposition); SC(NH2)2 (followed by hydrolysis with 10% NH4OH), PhCH2, HS, -, 136° (decomposition) [the product with PhCH2Cl and NH4OH at room temperature for 2 days, R’ = SCH2Ph, m. 51°, identical with the compound from PhCH2Cl and HSC:N.C(SH):N.S (VI)]; concentrated H2SO4 (warmed 3 hrs. and poured onto ice), Me, OH, 65%, 139-40°; KOH-MeOH, Me, OMe, 100, 46-7°. MeSC:N.S.C(SH):N (VII) oxidized 15 min. with 2N HNO3 at 50-60° gave [S.N:C(SMe).N:C]2S2, m. 112.5-13°; VII kept 5 hrs. at room temperature with the calculated amount of NH3 and MeI in EtOH gave V (R = Me, R’ = SMe), m. 40-1°, formed also from III (R = Me) with NH3 and excess MeSH in MeOH, and identical with the product from methylation of VI; VII kept several hrs. at room temperature with NH3-MeOH yielded almost 100% [S.N:C(SMe).N:C]2S, m. 169.5-70°. III (R = Me) (1.7 g.) refluxed 6 hrs. with NaOCMe:CHCO2Et (from 2 cc. AcCH2CO2Et kept 4 hrs. with 0.23 g. Na in 15 cc. dry C6H6), the resulting precipitate with the residue from the filtrate extracted with dilute NH4OH, and the extract acidified yielded 85% V [R = Me, R’ = HC(Ac)CO2Et] (VIII), m. 119-20° (decomposition). Similarly, with 2.9 cc. H2C(CO2Et)2 in place of AcCH2CO2Et was obtained 60% V [R = Me, R’ = HC(CO2Et)2] (IX), m. 143° (decomposition); and with 5 cc. NCCH2CO2Et and 0.5 g. Na 1.7 g. III (R = Me) yielded 80% V [R = Me, R’ = HC(CN)CO2Et], m. above 200°. III (R = Me) (3.65 g.) kept 24 hrs. with 5 cc. Ac2CH2 and 3.5 g. powd. K2CO3 in 25 cc. MeOH, then refluxed 6 hrs. on an H2O bath, kept overnight, the MeOH largely distilled, the residue warmed to 60-70° with 40 cc. H2O containing a little NH4OH, filtered, and the filtrate acidified yielded 35% V (R = Me, R’ = HCAc2), m. 144.5-5.0°. IX (2 g.) in 5-6 cc. 75% H2SO4 heated slowly to 130°, kept at 130° until no more gas evolved (4-6 min.), cooled, H2O added cautiously, and the mixture filtered after 3 hrs. yielded 70% V (R = Me, R’ = CH2CO2H), m. about 150-60° (decomposition) (Et ester, m. 70-1°), formed also from VIII (0.4 g.) with 5 cc. concentrated H2SO4. The experimental part of the paper was very detailed, including the reaction process of 5-Chloro-1,2,4-thiadiazole(cas: 38362-15-1Related Products of 38362-15-1)
5-Chloro-1,2,4-thiadiazole(cas: 38362-15-1) is a member of organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. They are generally not present in crude oils and are typically the result of additives, cleaning solutions or chemicals used for oil recovery.Related Products of 38362-15-1
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics