Synthesis
The reaction mixture was stirred at 100 °C for 8 hours with thiourea (50 mmol), 3-chloroacetophenone (25 mmol) and iodine (25 mmol). After completion of the reaction, the mixture was cooled and extracted with ether to remove unreacted 3-chloroacetophenone. Subsequently, it was washed with aqueous sodium thiosulfate to remove excess iodine and then with cold water. The crude product was dissolved in hot water and filtered to remove the sulfone by-product. The filtrate was alkalized with aqueous Na2CO3 to afford 2-amino-4-(3-chlorophenyl)-1,3-thiazole. Finally, the crude product was purified by recrystallization from alcohol.
References
[1] Chemical and Pharmaceutical Bulletin, 2007, vol. 55, # 7, p. 1014 - 1017
[2] European Journal of Medicinal Chemistry, 2013, vol. 66, p. 305 - 313
[3] Arzneimittel-Forschung/Drug Research, 1986, vol. 36, # 9, p. 1391 - 1393
[4] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 2, p. 692 - 702
[5] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 23, p. 5428 - 5431
