5-ADAMANTAN-1-YL-[1,3,4]THIADIAZOL-2-YLAMINE synthesis

Yield:26526-57-8 87%

Reaction Conditions:

with sulfuric acid at 5 - 25;

Steps:

2.3. Synthesis of 5-adamantyl-2-amino-1,3,4-thiadiazole

To well stirred and cooled (< 5 °C) concentrated sulfuric acid(10 mL), 1-(adamantyl-5-carboxy)thiosemicarbazide (1.1 g, 0.005 mol)was added in small portions. After the final addition the mixture wasstirred for a further 15 min and was then allowed to reach ambienttemperature (25 °C), left stirring for a further 30 min and then pouredcautiously onto crushed ice. The reaction mixture was alkalized to pH 8with aqueous ammonia and the precipitated product was filtered off,washed with water and recrystallized from CH3OH-CH2Cl2. Yield 87%.M.p. 200-201 °C. IR (cm-1, KBr): 3050 (NH). 1H NMR: (δ ppm, DMSO,500 MHz): 1.70-2.01 (m, 15Η, adamant.), 7.01 (s, 2Η, -ΝΗ2).

References:

Fesatidou, Maria;Zagaliotis, Panagiotis;Camoutsis, Charalampos;Petrou, Anthi;Eleftheriou, Phaedra;Tratrat, Christophe;Haroun, Micheline;Geronikaki, Athina;Ciric, Ana;Sokovic, Marina [Bioorganic and Medicinal Chemistry,2018,vol. 26,# 16,p. 4664 - 4676]