Back to results
US 6,187,927 B1Granted
Process for preparing a 2-chloro-5-chloromethyl-thiazole compound
AssigneeNovartis Crop Protection, Inc.
InventorThomas Pitterna
Life of this patent
Estimating the term…
Abstract
The invention relates to a process for preparing a compound of formula (I) in which A is chlorine or 3-methyl-4-nitroimino-perhydro-1,3,5-oxadiazin-5-yl; to intermediates used in this process; to the use of these intermediates; and to a process for the preparation of these intermediates. The compounds of formula (I) are valuable intermediates in the process of preparing pesticidal, especially insecticidal or acaricidal, formulations.
Claims9
A process for preparing a compound or the formula
- in which A is chlorine of 3-methyl-4-nitroimino-perhydro-1,3,5-oxadiazin-5-yl, which process comprises
- a) reacting a compound of the formula
- in which X is a leaving group, optionally in the presence of a base, with a dehydrating agent, a halogenating agent, and a sulfurizing agent, to give the compound of the formula I, in which A is chlorine, or
- b1) reacting a compound of the formula II, optionally in the presence of a base, with a dehydrating agent to give a compound of the formula
- in which X is as defined for the formula II, and
- b2) reacting the compound thus obtainable of the formula III with a halogenating agent and a sulfurizing agent, optionally in the presence of a base or acid, to give the compound of the formula I, in which A is chlorine, or
- c) reacting a compound of the formula
- in which X is as defined for the formula II, with a compound of the formula
- HC(R1)(R2)R3 V,
- in which either R1and R2 together are oxo and R3 is hydroxy, C1-C6alkoxy or N(R4)R5, R4 and R5 being, independently of one another, hydrogen or C1-C6alkyl, or R1, R2 and R3, independently of one another, are C1-C6alkoxy, to give a compound of the formula II and reacting the compound thus obtainable of the formula II either in accordance with the process variant a) or in accordance with the process variant b1)/b2) to give the compound of the formula I, in which A is chlorine, or
- d) preparing the compound of the formula I, in which A is chlorine, either in accordance with the process variant a) or in accordance with the process variant b1)/b2) or in accordance with the process variant c) and reacting the compound thus obtainable of the formula I, in which A is chlorine, optionally in the presence of a base, with 3-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine or with 3-methyl-4-nitroamino-3,3-dihydro-6H-1,3,5-oxadiazine, to give the compound of the formula I, in which A is 3-methyl-4-nitroimino-perhydro-1,3,5-oxadiazin-5-yl.
8 more elements
Dependencies are inferred from the claim text.