The author of 《1,2,4-Thiadiazoles. VIII. The synthesis of 5-chloro-1,2,4-thiadiazoles from perchloromethylmercaptan and amidines》 were Goerdeler, Joachim; Groschopp, Heinz; Sommerlad, Ursula. And the article was published in Chemische Berichte in 1957. Application In Synthesis of 5-Chloro-1,2,4-thiadiazole The author mentioned the following in the article:
cf. C.A. 51, 8731c. Adding dropwise (about 7 hrs.) with vigorous stirring 100 g. NaOH in 150 cc. H2O to 47 g. MeC(:NH)NH2.HCl and 83 g. CCl3SCl in 500 cc. CH2Cl2 at -8°, extracting the aqueous layer with CH2Cl2, and fractionally distilling the washed and dried CH2Cl2 solution give 60% N:CR.N:CR’.S (Ia) (R = Me, R’ = Cl) (I), b18 45°, b21 51°, nD22.5 1.52075, d20 1.355; 68% Ia (R = Et, R’ = Cl) (II), b17 60°, nD24 1.5129, d20 1.203. Adding 1.6 g. NaOH in 50 cc. H2O to 1.8 g. PhC(:NH)NH2.HCl.H2O and 1.8 g. CCl3SCl in 50 cc. H2O and a small amount of Na dodecylsulfate at below 10° and stirring the mixture 15 min. give 80% Ia (R = Ph, R’ = Cl), b3 115°, b12 136°, prisms, m. 52°; 45% Ia (R = PhCH2, R’ = Cl), b1.5 105-7°, b3 122-3°, m. 3-4°, nD19 1.5904, d16 1.305. Warming 4.5 g. II in 20 cc. concentrated H2SO4 1.5 hrs. on a H2O bath, pouring the mixture into ice-H2O, and extracting with Et2O give 85% Ia (R = Et, R’ = OH), needles, m. 89°; 90% Ia (R = Ph, R’ = OH), small rods, m. 204-6° (decomposition); 94% Ia (R = PhCH2, R’ = OH), leaflets, m. 106-7°. Adding 0.23 g. Na in 25 cc. MeOH to 1.96 g. II in 50 cc. MeOH, evaporating the filtered solution, and extracting the residue with Et2O yield Ia (R = Ph, R’ = OMe), leaflets, m. 32.5°; Ia (R = PhCH2, R’ = OMe), b2 124-5°, nD20 1.5713, d16 1.213; 100% Ia (R = Ph, R’ = EtO), b1.5 120-1°, nD20 1.5910, d16 1.206; 90% Ia (R = PhCH2, R’ = OEt), b1.26 118-20°, nD20 1.5584, d16 1.168; 36% Ia (R = Me, R’ = OEt), b19 71°, nD22.5 1.4898, d20 1.1521. Heating 5.4 g. I in 8 cc. EtOH with 3 g. CS(NH2)2 1.5 hrs. on a H2O bath, adding 50 cc. H2O and 5 cc. 33% KOH, boiling the mixture 5 min., acidifying the filtered solution with concentrated HCl, and extracting with Et2O yield 75% Ia (R = Me, R’ = SH), slightly yellow crystals, m. 151°; 72% Ia (R = Et, R’ = SH), m. 149° (decomposition). Treating 2.7 g. I in 5 cc. EtOH 2 hrs. with 25 cc. alc. MeNH2 solution, evaporating the solution, and extracting the residue with Et2O give 97% Ia (R = Me, R’ = NHMe), m. 96°; Ia (R = Et, R’ = NHMe), needles, m. 70°. The acidity constants of some of the compounds have been determined5-Chloro-1,2,4-thiadiazole(cas: 38362-15-1Application In Synthesis of 5-Chloro-1,2,4-thiadiazole) was used in this study.
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.Application In Synthesis of 5-Chloro-1,2,4-thiadiazole
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics