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US 6,642,418 B1Granted
Processes for preparing intermediates
AssigneeAventis CropScience GmbH
InventorsSusan Mary Cramp, Neil Jonathan Geach
Life of this patent
Estimating the term…
Abstract
The invention relates to processes for the preparation of compounds of formula (I), wherein R1 and R2 are as defined in the description.
Claims20
A process for the preparation of a compound of formula (I):
- wherein:
- one of the groups R1 and R2 is cyclopropyl and the other is phenyl substituted by two or three groups, which may be the same or different selected from halogen, nitro, cyano, —(CR4R5)S(O)pR6, —S(O)pR6, C1-6alkoxy, C1-4haloalkoxy, C1-4alkyl, C1-4haloalkyl, 1,2,4-triazol-1-yl and —SF5;
- wherein:
- p is zero, one or two;
- R4 and R5 are independently hydrogen or C1-4alkyl;
- and
- R6 is C1-4alkyl;
- which process comprises the hydrolysis and decarboxylation of a compound of formula (II):
- wherein R1 and R2 are as hereinbefore defined, and R3 is C1-4alkyl, in the presence of water.
6 more elements
A process for the preparation of a compound of formula (II):
- wherein one of the groups R1 and R2 is cyclopropyl and the other is phenyl substituted by two or three groups, which may be the same or different selected from the group consisting of halogen, nitro, cyano, —(CR4R5)S(O)pR6, —S(O)pR6, C1-6alkoxy, C1-4haloalkoxy, C1-4alkyl, C1-4haloalkyl, 1,2,4-triazol-1-yl and —SF5;
- and R3 is C1-4alkyl comprising acylating a compound of formula III:
- with a compound of formula (IV):
- R2C(═O)X (IV)
- wherein X is a leaving group, wherein said process is performed using a magnesium halide in the presence of a base.
2 more elements
A process for the preparation of a compound of formula (III):
- wherein R1 is cyclopropyl or phenyl substituted by two or three groups, which may be the same or different selected from the group consisting of halogen, nitro, cyano, —(CR4R5)S(O)pR6, —S(O)pR6, C1-6alkoxy, C1-4haloalkoxy, C1-4alkyl, C1-4haloalkyl, 1,2,4-triazol-1-yl and SF5;
- wherein:
- p is zero, one, or two;
- R4 and R5 are independently hydrogen or C1-4alkyl;
- and
- R6 is C1-4alkyl;
- and
- R3 is C1-4alkyl,
- comprising reacting a compound of formula (V):
- wherein Y is a leaving group, with a compound of formula (VI):
- via the decarboxylation of a compound of formula (VII):
8 more elements
A compound having the formula (II):
- wherein one of the groups R1 and R2 is cyclopropyl and the other is phenyl substituted by two or three groups, which may be the same or different selected from the group consisting of halogen, nitro, cyano, —(CR4R5)S(O)pR6, —S(O)pR6, C1-6alkoxy, C1-4haloalkoxy, C1-4alkyl, C1-4haloalkyl, 1,2,4-triazol-1-yl and —SF5;
- wherein:
- p is zero, one, or two;
- R4 and R5 are independently hydrogen or C1-4alkyl;
- and
- R6 is C1-4alkyl;
- and R3 is C1-3alkyl.
4 more elements
Dependencies are inferred from the claim text.