p-Bis(2-chloroethyl)aminophenylalanine (sarcolysine) and its derivatives. VI. Amides of N-acetylsarcolysine and some amines of the thiazole series was written by Berlin, A. Ya.;Bronovitskaya, V. P.. And the article was included in Zhurnal Obshchei Khimii in 1961.Category: thiazole This article mentions the following:
Heating thiazole with 40% HCHO in an autoclave 6 hrs. at 120° gave (after treatment with aqueous K2CO3 then 1:1 HCl) 22.5% 2-(hydroxymethyl)thiazole-HCl, m. 126.5-7°, which with SOCl2 in CHCl3, finally at reflux 1.5 hrs., gave 77% 2-(chloromethyl)thiazole, b5 62° (picrate m. 126.5-7.5°). Crude 5-(hydroxymethyl)thiazole gave HCl salt, m. 83-4°, which with SOCl2 gave 78.6% 5-(chloromethyl)thiazole, isolated as picrate, m. 103-4°; free base, undistilable oil. The chloromethyl derivatives with o-C6H4(CO)2NK in 2 hrs. at 150-80° gave 2-phthalimidothiazole, m. 117-18°, 4-isomer, m. 157-8°, and 2-methyl-4-phthalimidothiazole, m. 146-6.5°, in 58-63% yield. These refluxed in EtOH with N2H4.H2O gave 2-(aminomethyl)thiazole, b14 93-5° (HCl salt m. 186-7°), 4-(aminomethyl)thiazole-HCl, m. 212-13°, and 2-methyl-4-(aminomethyl)thiazole, b22 106-7°, n20D 1.553. The 5-(chloromethyl)thiazole was very unstable and its reaction with K phthalimide failed to give a definite product. Treatment of N-acetylsarcolysine with the aminomethylthiazoles in CHCl3 in the presence of dicyclohexylcarbodiimide (cf. loc cit.) gave N-acetylsarcolysine 2-thiazolylmethylamide, m. 174.5-5.5°, 4-thiazolylmethylamide, m. 160-1°, 2-methyl-4-thiazolylmethylamide, m. 141-2°, and 5-thiazolylamide, m. 210-11°. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Category: thiazole).
Thiazol-2-ylmethanamine (cas: 55661-33-1) 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. Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Category: thiazole
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica