Definition
ChEBI: A member of the class of guanidines that is tetrahydropyrimidin-2(1H)-imine in which the hydrogen of the imino group is replaced by a thiazol-2-yl group which in turn is substituted by a 2-(2,4-dimethylphenoxy)phenyl group at position 4
It has been used for the topical treatment of fungal nail infections.
Manufacturing Process
15.8 g (0.12 mole) N-(1,4,5,6-tetrahydropyrimidinyl)thiourea were added to
27.45 g (0.1 mole) 2-(2,4-dimethylphenoxy)phenacyl chloride in 100 ml
acetone and heated to reflux for 2 hours. On cooling the falling out product
was filtered off, washed with acetone and dried. N-[4-[2-(2,4-
Dimethylphenoxy)phenyl]-2-thiazolyl]-1,4,5,6-tetrahydro-2-pyrimidinamine
hydrochloride was prepared. Yield 91.4%; MP: 160°C.
20.72 g (0.05 mole) above product was stirred with 300 ml 1 N sodium
hydroxide for 30 minutes at room temperature. The insoluble product was
filtered off, washed and dried. Yield of N-[4-[2-(2,4-dimethylphenoxy)phenyl]-
2-thiazolyl]-1,4,5,6-tetrahydro-2-pyrimidinamine was 16.2 g (86%). MP:
191°-192°C.
