Syntheses of new sulfonamides. VIII. Syntheses of new hypoglycemic sulfonamides related to 2-sulfanilamido-5- isopropyl-1,3,4-thiadiazole was written by Takatori, Kichitaro;Yamada, Yasuo;Asano, Shingo. And the article was included in Yakugaku Zasshi in 1959.Application In Synthesis of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride This article mentions the following:
The following RSO2Cl are prepared (R and m.p. given): p-AcNHC6H4, 149°; p-MeAcNC6H4, 126°; 3,4-Me(AcNH)C6H3, 159°; 4,3-Me(AcNH)C6H3, 142°; p-O2NC6H4, 80°; Ph, 14.5°; p-MeC6H4, 69°; 3,6-Me2C6H3, 24-6°; p-EtOCO2C6H4, 71°, 6,2-EtOCO2C10H6, 118°; p-FC6H4, 53°; p-BrC6H4, 76°; 2-acetamido-4-methyl-5-thiazolyl, 157° (decomposition). NH2CSNHNH2 (1 mole) and 2 moles corresponding acid chloride refluxed 1 hr., the product at 80-90° extracted with dilute HCl and made alk. with NH4OH or Na2CO3 gave 2-amino-5-alkyl-1,3,4-thiadiazole (alkyl group and m.p. given): Me, 235°; Et, 196°; Pr, 203°; iso-Pr, 187°; Bu, 196°; iso-Bu, 229°; Am, 195°; undecyl, 115°. 2-Amino-5-isopropyl-1,3,4-thiadiazole (I) (0.1 mole) in 140 ml. C5H5N was heated 1 hr. at 100° with 0.1 mole p-AcNHC6H4SO2Cl, the C5H5N removed and the residue treated with 100 ml. 10% HCl to give 28.4 g. 2-(p-AcNHC6H4SO2NH) analog (II) of I, m. 183-4° (EtOH). II (28.4 g.) in 200 ml. 10% NaOH heated 1 hr. at 100° and the product recrystallized (H2O) gave 15.4 g.2-(p-H2NC6H4SO2NH) analog of I, m. 195°. Similarly are prepared 2-RSO2NH analogs of I (R and m.p. given): p-MeNHC6H4, 141°; 3,4-Me(H2N)C6H3, 175°; 4,3-Me(H2N)C6H3, 163°; p-HOC6H4, 100°; p-MeC6H4 (monohydrate), 93° (decomposition); 2,5-Me2C6H3, 120°; p-O2NC6H4, 172°; p-FC6H4, 97-9°; p-ClC6H4, 133°; p-BrC6H4, 142°; Ph, 125°; 2-acetamido-4-methyl-5-thiazolyl, 255-7° (decomposition). Condensation of equimolar amounts of 2-amino-5-alkyl-1,3,4-thiadiazole and p-MeC6H4SO2Cl in C5H5N yielded 2-(p-toluenesulfonamido)-5-alkyl-1,3,4-thiadiazole (alkyl group and m.p. given): Me, 198°; Et, 130°; Pr, 139°; iso-Pr, 108°; Bu, 114°; Me2CHCH2, 175°; Am, 128°; Me(CH2)10, 92°. The sulfonamides of this series which have the power to reduce blood sugar level are generally soluble in dilute alk. carbonate, similar to N-acylated arenesulfonamides. This property was utilized for their purification. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Application In Synthesis of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride).
2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) belongs to thiazole derivatives. The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone. 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.Application In Synthesis of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica