With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.302964-20-1,tert-Butyl (5-(chlorocarbonyl)thiazol-2-yl)carbamate,as a common compound, the synthetic route is as follows.
Into a clean and dry 3L 4-neck round bottom flask connected to a mechanical stirrer,condenser and thermometer socket is charged with 2-tert-butoxycarbonylamino-thiazole-5-carboxylic acid chloride (4) crude (27.5 g) and dichloromethane (750 mL) under stirring. Cooled the reaction mass to 0-5 C and add 2-chloro-6-methylaniline (22.2 g) to the reaction mass at 0-5 C within 30-45 min period. Added DiPEA to the reaction mass at 0-5 C in 30-45 min period, raised the reaction mass temperature to 25-30 C and stirred the reaction mass at 25-30 C for 24 h. After TLC compliance distilled-off the solvent completely under plant vacuum at the temperature not crossing 50 C and Charge 2 N HCl (250 mL) to the reaction mass, Stirred for 15-30 min. Transferred the reaction mass into a Buchner funnel and flask kept under plant vacuum. The wet cake is washed with 500mL of water and dried the above-wet material in the dryer at temperature 60-65 C for 10-12 h. Purification: Into a clean and dry 3.0 L 4-neck round bottom flask connected to a mechanical stirrer, condenser, thermometer socket is charging with 2-tert-butoxy-carbonyl-amino-N-(2-chloro-6-methylphenyl)-5-thiazolecarboxamide crude, methanol and isopropyl ether under stirring at 25- 30 C. Raised the reaction mass temperature to 60-65 C and stirred the reaction mass at 60-65 C for 45-60 min. Cooled the reaction mass temperature to 25-30 C and transferred the reaction mass into a Buchner funnel and flask kept under plant vacuum. Washed the wet cake with 20.0 mL of methanol and dried the wet material in dryer at 60-65 C for 4-6 h to furnish 16.0 g of the title compound with purity above 95 %. Cream colour solid; Elemental analysis C16H18N3O3SClcalcd (found) %: C 52.24 (52.12), H 4.93 (5.05), N 11.42 (11.31),O 13.05 (13.25), S 8.72 (8.83). IR (KBr, numax, cm-1): 3423.42-3276.87, 3162.67, 2928.46, 1724.90, 1632.68-1566, 1522.80,775.21; 1H NMR (400 MHz, DMSO-d6): delta1.504 (s, 9H, -3CH3),2.225 (s, 3H, -CH3), 7.262-7.301 (t, 2H, ArH), 7.389-7.412(m, 1H, ArH), 8.204 (s, 1H, ArH), 10.017 (s, 1H, -NH), 11.847(s, 1H, -NH); 13C NMR (100 MHz, DMSO-d6): delta163.220, 159.74,152.91, 141.27, 139.02, 133.31, 132.57, 129.34, 128.64, 127.28,126.62, 82.33, 28.06, 18.45; ESI-MS (m/z): 368.21 (M+1),370.18 (M+3)
302964-20-1 tert-Butyl (5-(chlorocarbonyl)thiazol-2-yl)carbamate 45117870, athiazole compound, is more and more widely used in various.
Reference£º
Article; Buchappa; Sagar Vijay Kumar; Durga Prasad; Aparna; Asian Journal of Chemistry; vol. 30; 7; (2018); p. 1621 – 1628;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica