Process for the preparation of 2-amino-4-chloro-1,3,5-triazines
AssigneeAventis CropScience GmbH
InventorsJürgen Zindel, Jens Hollander, Klemens Minn, Lothar Willms
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Abstract
Compounds of the formula (I) or salts thereof are suitable for preparing active substances from the from the class of the aminotriazines of the formula (IV), for example herbicidal active substances. The compounds (I) can be prepared by chlorinating compounds of the formula (II) where, in the formulae, R1, R2, R3 and X are as defined in claim 1 and A and R have the meaning required in the active substances to be prepared, and they can be reacted with amines of the formula A—NH—R to give the active substances.
Claims18
A process for the preparation of compounds of the formula (I) or salts thereof
- in which
- R1 is (C1–C8)alkyl or (C3–C8)cycloalkyl, which is independently of one another unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, nitro, thiocyanato, formyl, (C1–C8)alkoxy, (C1–C8)alkylthio, (C1–C8)alkylsulfinyl, (C1–C8)alkylsulfonyl, [(C1–C8)-alkyl]carbonyl, [(C1–C8)alkoxy]carbonyl, (C3–C8)cycloalkyl, phenyl and, in the case of cycloalkyl, also (C1–C8)alkyl, each of the last-mentioned 9 radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1–C4)alkoxy, (C1–C4)alkylthio and, in the case of cyclic radicals, also (C1–C4)alkyl and (C1–C4)haloalkyl, and
- R2,R3 in each case independently of one another are hydrogen, amino, (C1–C6)alkyl, (C1–C4)alkylamino, di[(C1–C4)alkyl]amino, (C1–C4)alkyloxy, (C3–C6)cycloalkyl, [(C1–C4)alkyl]carbonyl, [(C1–C4)alkoxy]carbonyl, phenylcarbonyl, phenoxycarbonyl, (C1–C4)alkylsulfonyl, phenylsulfonyl or a saturated heterocyclyl radical having 3 to 6 ring atoms and 1 to 3 hetero ring atoms selected from the group consisting of N, O and S, where phenyl in the abovementioned radicals or the heterocyclyl radical independently of one another are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, (C1–C4)alkoxy, (C1–C4)alkyl, and (C1–C4)haloalkyl, or
- R2,R3 together with the nitrogen atom of the group NR2R3 is a saturated heterocyclic radical which has 3 to 6 ring atoms and 1 to 3 hetero ring atoms, where, in addition to the nitrogen atom, the other hetero ring atoms which may be present are selected from the group consisting of N, O and S and the heterocycle is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, (C1–C4)alkoxy, (C1–C4)alkyl and (C1–C4)haloalkyl,
- which comprises converting 2-amino-4-thio-1,3,5-triazines of the formula (II)
- in which X represents (C1–C4)alkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1–C4)alkoxy, (C1–C4)alkylthio, (C3–C6)cycloalkyl and phenyl, each of the last-mentioned 4 radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1–C4)alkoxy, (C1–C4)alkylthio and, in the case of cyclic radicals, also (C1–C4)alkyl and (C1–C4)haloalkyl, or represents phenyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, (C1–C4)alkyl, (C1–C4)haloalkyl, (C1–C4)alkoxy, (C1–C4)haloalkoxy, (C1–C4)alkylthio and [(C1–C4)alkoxy]carbonyl, or represents a 2-amino-4-thio-1,3,5-triazine radical which is bonded via sulfur and equally substituted, by chlorination in the presence of an essentially anhydrous protic solvent.
Dependencies are inferred from the claim text.