Process for production of (4,5-dihydroisoxazol-3-Y) thio-carboxamidine salts
To provide a method for producing a (4,5-dihydroisoxazol-3-yl)thiocarboxamidine salt compound simply, safely and in good yield, whereby drawbacks of prior art have been solved. A method for producing a (4,5-dihydroisoxazol-3-yl)thiocarboxamidine salt compound of the formula (2): wherein each of R 1 and R 2 which are independent of each other, is a hydrogen atom, an alkyl group or a cycloalkyl group, each of R 3 and R 4 which are independent of each other, is a hydrogen atom or an alkyl group, provided that R 1 and R 2 , or R 2 and R 3 , may be bonded to each other to form a cycloalkyl group together with the carbon atoms to which they are bonded, and X 2 is a halogen or an anionic residue derived from an acid, which comprises reacting a 3-halogeno-4,5-dihydroisoxazole compound of the formula (1): wherein R 1 , R 2 , R 3 and R 4 are as defined above, and X 1 is a halogen, with thiourea in the presence of an acid.
1. A method for producing a (4,5-dihydroisoxazol-3-yl)thiocarboxamidine salt compound of formula (2):
wherein each of R 1 and R 2 which are independent of each other is a hydrogen atom, an alkyl group or a cycloalkyl group, each of R 3 and R 4 which are independent of each other, is a hydrogen atom or an alkyl group, provided that R 1 and R 2 , or R 2 and R 3 may be bonded to each other to form a cycloalkyl group together with the carbon atoms to which they are bonded, and X 2 is a halogen or an anionic residue derived from an acid, which method comprises reacting a 3-halogeno-4,5-dihydroisoxazole compound of formula (1):
wherein R 1 , R 2 , R 3 and R 4 are as defined above, and X 1 is halogen with thiourea in the presence of an acid.
2. The method for producing a (4,5-dihydroisoxazol-3-yl)thiocarboxamidine salt compound according to claim 1 , wherein the acid is inorganic acid.
3. The method for producing a (4,5-dihydroisoxazol-3-yl)thiocarboxamidine salt compound according to claim 1 , wherein the acid is hydrochloric acid hydrobromic acid or a mixture thereof.
4. The method for producing a (4,5-dihydroisoxazol-3-yl)thiocarboxamidine salt compound according to claim 1 , wherein in formula (1), each of R 1 and R 2 is an alkyl group, each of and R 3 and R 4 is a hydrogen atom, and X 1 is a chlorine atom.
5. The method for producing a (4,5-dihydroisoxazol-3-yl)thiocarboxamide salt compound according to claim 1 , wherein in formula (1), each of R 1 and R 2 is a methyl group, each of R 3 and R 4 is a hydrogen atom, and X 1 is a chlorine atom.
6. The method for producing a (4,5-dihydroisoxazol-3-yl)thiocarboxamidine salt compound according to claim 1 , wherein in formula (1), each of R 1 and R 2 is an alkyl group each of R 3 and R 4 is a hydrogen atom, and X 1 is a bromine atom.
7. The method for producing a (4,5-dihydroisoxazol-3-yl)thiocarboxamidine salt compound according to claim 1 , wherein in formula (1), each of R 1 and R 2 is a methyl group, each of R 3 and R 4 is a hydrogen atom, and X 1 is a bromine atom.
8. A (4,5-dihydroisoxazol-3-yl)thiocarboxamidine salt compound of formula (2):
wherein each of R 1 and R 2 , which are independent of each other, is a hydrogen atom, an alkyl group or a cycloalkyl group, each of R 3 and R 4 which are independent of each other is a hydrogen atom or an alkyl group provided that R 1 and R 2 , or R 2 and R 3 , may be bonded to each other to form a cycloalkyl group together with the carbon atoms to which they are bonded, and X 2 is a halogen or an anionic residue derived from an acid.
9. A (4,5-dihydroisoxazol-3-yl)thiocarboxamidine salt or compound of formula (3):
wherein each of R 1 and R 2 , which are independent of each other is hydrogen atom, an alkyl group or a cycloalkyl group each of R 3 and R 4 , which are independent of each other is a hydrogen atom or an alkyl group, provided that R 1 and R 2 , or R 2 and R 3 , may be bonded to each other to form a cycloalkyl group together with the carbon atoms to which they are bonded, and X 3 is a halogen.
10. The (4,5-dihydroisoxazol-3-yl)thiocarboxamidine salt compound according to claim 8 , wherein each of R 1 and R 2 is a methyl group, and each of R 3 and R 4 is a hydrogen atom.
11. The (4,5-dihydroisoxazol-3-yl)thiocarboxamidine salt compound according to claim 9 , wherein each of R 1 and R 2 is a methyl group, and each of R 3 and R 4 is a hydrogen atom.
12. [5,5-dimethyl-(4,5-dihydroisoxazol-3-yl)]thiocarboxamidine hydrochloride.
13. [5,5-dimethyl-(4,5-dihydroisoxazol-3-yl)]thiocarboxamidine hydrochloride.