Claims
- 1. A process for the preparation of a guanidine derivative of the formula ##STR525## in which R.sub.1 represents hydrogen or the radical R.sup.5 --S(O).sub.m --,
- m represents the numbers zero, 1 or 2 and
- R.sup.5 represents a radical selected from the group consisting of alkyl aralkyl, pyridyl, quinolinyl, furyl, thienyl and pyrrolyl,
- R.sup.2 represents a six-membered aromatic heterocyclic structure selected from the group consisting of pyridyl, pyrimidinyl and 1,3,5-triazinyl and which is substituted by halogen, amino, cyano or formyl and/or by optionally substituted radicals from the group consisting of alkyl, alkoxy, alkylamino, dialkylamino, alkylcarbonyl and alkoxycarbonyl, and
- R.sup.8 represents an optionally substituted radical from the group consisting of C.sub.1 -C.sub.6 -alkyl, alkenyl, alkinyl, cycloalkyl, phenylallkyl and aryl,
- which comprises reacting a guanidine derivative of the formula ##STR526## with one or two molar equivalent(s) respectively, of a halogen/sulphur compound of the formula
- R.sup.5 --S(O).sub.m --X.sup.1
- in which
- X.sup.1 represents fluorine, chlorine or bromine.
- 2. A process according to claim 1 for the preparation of a guanidine derivative of the formula ##STR527## which comprises reacting a guanidine derivative of the formula ##STR528## with about an equimolar amount of
- R.sup.5 --S(O).sub.m --X.sup.1.
- 3. A process according to claim 1 for the preparation of a guanidine derivative of the formula ##STR529## which comprises reacting a guanidine derivative of the formula ##STR530## with at least two molar equivalents of
- R.sup.5 --S(O).sub.m --X.sup.1
- or reacting a guanidien derivative of the formula ##STR531## with at least one molar equivalent of
- R.sup.5 --S(O).sub.m --X.sup.1.
- 4. The process according to claim 1, wherein R.sup.5 --S(O).sub.m --X.sup.1 is selected from the group consisting of 2-chloro-, 2-fluoro-, 2-bromo-, 2-nitro-, 2-methyl-, 2-methoxycarbonyl-, 2-ethoxycarbonyl-, 2-methoxy-, 2-ethoxy-, 2-phenyl-, 2-trifluoromethyl-, 2-difluoromethoxy-, 2-trifluoromethoxy-, 2-phenoxy-, 2-methyl-5-chloro-, 2,5-dichloro- and 2-chloro-5-trifluoromethyl-benzenesulphonyl chloride.
- 5. The process according to claim 1, wherein the reaction is effected in an organic solvent.
- 6. The process according to claim 1, wherein the reaction is effected in an aprotic polar solvent.
- 7. The process according to claim 1, wherein the reaction is effected in at least one solvent selected from the group consisting of a hydrocarbon, a halogenated hydrocarbon, a nitrile, dimethyl formamide, dimethyl acetamide, dimethyl sulphoxide, sulpholane, hexamethylphosphoric acid triamide, 1,2-dimethoxyethane, pyridine and 2-methyl-5-ethylpyridine.
- 8. The process according to claim 1, wherein the reaction is effected in the presence of an acid-binding agent.
- 9. The process according to claim 1, wherein the reaction is effected in the presence of an acid-binding agent selected from the group consisting of alkali metal and alkaline earth metal hydroxides or hydrides, organometallic compounds, and organic amines.
- 10. The process according to claim 1, wherein the reaction is effected in the presence of an acid-binding agent selected from the group consisting of trimethylamine, triethylamine, N,N-dimethylaniline, N,N-dimethyl-benzylamine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), pyride and 2-methyl-5-ethyl-pyridine.
- 11. The process according to claim 1, wherein the reaction is effected in the presence of diazabicyclooctane (DABCO) as an acid-binding agent.
Priority Claims (2)
Number |
Date |
Country |
Kind |
3307679 |
Mar 1983 |
DEX |
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3334455 |
Sep 1983 |
DEX |
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Parent Case Info
This is a continuation-in-part of application Ser. No. 853,822, filed Apr. 18, 1986, now U.S. Pat. No. 4,721,785, which is a division of application Ser. No. 578,345, filed Feb. 9, 1984, now U.S.Pat. No. 4,602,938.
Non-Patent Literature Citations (3)
Entry |
Merck et al., 9th Ed., 1976, ONR-44 (Hinsberg Synthesis). |
Desulfurization with Raney Nickel. II. Sulfonamides.sup.1,2, George R. Pettit and Raymond E. Kadunce, J. Org. Chem., vol. 27 (Dec. 1962), pp. 4566-4570. |
J. Org. Chem, vol. 39, No. 24 (1974), DeChristopher, Adamek, Lyon, Klein and Baumgauten, pp. 3525-3532. |
Divisions (1)
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Number |
Date |
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Parent |
578345 |
Feb 1984 |
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Continuation in Parts (1)
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Number |
Date |
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Parent |
853822 |
Apr 1986 |
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