Journal of the Chemical Society published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, HPLC of Formula: 5053-24-7.
Batty, J. W. published the artcileAcetylene reactions. III. Reaction of aminobutynes with carbon disulfide, HPLC of Formula: 5053-24-7, the publication is Journal of the Chemical Society (1949), 786-9, database is CAplus.
Addition of 10 cc. CS2 to 11.1 g. iso-PrNHCHMeCCH (I), 4 g. NaOH, and 30 cc. H2O at 50°, with stirring for an addnl. 2 hrs., gives 58% 4-methyl-3-isopropyl-5-methylene-2-thiazolidinethione (II), MeCH.C(:CH2).S.CS.NCHMe2, b0.4 130-5°, m. 43°. II results in 8-g. yield on refluxing 4 hrs. 10.6 g. I and 10 cc. CS2 in 50 cc. EtOH. II with O3 gives HCHO. BuNHCHMeCCH (12.5 g.) yields 87% of the 3-Bu homolog of II, b0.5, 140-2°, nD16 1.5975. 3-Cyclohexyl analog of II, b0.15 150-60°, m. 69-70°. 3-Benzyl analog, pale yellow, b0.075 165-75°. (iso-PrNHCHMeCC)2 (5 g.) yields 2.5 g. 1,2-bis(4-methyl-3-isopropyl-2-thiono-5-thiazolyl)ethane, [S.CS.N(CHMe2).CMe:CCH2]2, m. 270° (decomposition). Solution of 2.5 g. II in cold concentrated H2SO4 gives 2 g. 4,5-dimethyl-3-isopropyl-2(3H)-thiazolethione (III), m. 84-6°; III results in 7.2-g. yield from 9 g. MeCHBrAc with 4.85 g. CS2 and 7.5 g. iso-PrNH2 in 25 cc. EtOH. 3-Bu homolog of III, pale yellow, m. 42-4°; cyclohexyl analog (IV), m. 104°; benzyl analog, m. 111°. CS2 (19.5 g.) and 30 g. iso-PrNH2 in 100 cc. EtOH, treated (0.5 hr.) with ClCH2Ac, give 26 g. 4-methyl-3-isopropyl-2(3H)-thiazolethione, m. 68-9°; 13 g. 2-ClCH2CH2Ac gives 21 g. 10-3-ketobutyl isopropyldithiocarbamate, m. 62°; this is not cyclized by treatment with cold concentrated H2SO4 or on heating in EtOH. 2-Cyclohexylamino-3-butyne (20 g.), on hydrogenation in MeOH over Raney Ni, gives 15 g. N-cyclohexyl-sec-butylamine (V), b25 86-8°, nD16 1.4350 (HCl salt, m. 210°); 10 g. V, 9 g. MeI, and 5 g. KOH, heated 2 hrs. on the steam bath and the base in dilute HCl treated with a slight excess of saturated aqueous NaNO2, give 4.5 g. N-cyclohexylmethyl-sec-butylamine (VI), b22 90-3° (methiodide, m. 174-6°); 3 g. IV and 20 cc. Raney Ni in 80 cc. EtOH, refluxed 4 hrs., give 0.4 g. VI. MeNHCH2CH2OH (5 g.) in 7 cc. CS2, heated 3.5 hrs. at 120-40°, gives 5.8 g. 3-methyl-2-thiazolidinethione, b. 90-100 °/10-4 mm. (bath), m. 68-9°; with MeI it yields 2-(methylmercapto) thiazoline-MeI, m. 132°. BuNHCH2CH2OH (5 g.) and 5 cc. CS2, heated 3.5 hrs. at 120-40°, give 4.9 g. 3-butyl-2-thiazolidinethione, yellow, b. 90-5°/10-4 mm. (bath), nD22.5 1.5970.
Journal of the Chemical Society published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, HPLC of Formula: 5053-24-7.
Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica