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US 6,320,059 B1Granted
Process for the preparation of 2-aryl-5-(perfluoro-alkyl) pyrrole compounds from N-[1-chloro-1-(perfluoroalkyl) methyl] arylimidoyl chloride compounds
AssigneeAmerican Cyanamid Company
InventorVenkataraman Kameswaran
Life of this patent
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Abstract
There is provided a process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from N-[1-chloro-1-(perfluoroalkyl)methyl]arylimidoyl chloride compounds. The 2-aryl-5-(perfluoroalkyl)pyrrole compounds are useful for the control of insect and acrid pests, and may also be used to prepare other pesticidal arylpyrrole compounds. In addition, the present invention provides compounds which are useful as intermediates in the preparation of arylpyrrole compounds.
Claims11
A process for the preparation of a 2-aryl-5-(perfluoroalkyl)pyrrole compound having the formula I
- wherein
- W is hydrogen or CmF2m+1;
- Y is CN, NO2 or CO2R;
- R is C1-C4alkyl;
- m and n are each independently an integer of 1, 2, 3, 4, 5, 6, 7 or 8;
- A is
- or
- L is hydrogen or halogen;
- M and Q are each independently hydrogen, halogen, CN, NO2, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulfinyl, C1-C4haloalkylsulfinyl, C1-C4alkylsulfonyl or C1-C4haloalkylsulfonyl, or when M and Q are on adjacent positions they may be taken together with the carbon atoms to which they are attached to form a ring in which MQ represents the structure —OCH2O—, —OCF2O— or —CH═CH—CH═CH—;
- R1, R2 and R3 are each independently hydrogen, halogen, NO2 or CHO, or R2 and R3 may be taken together with the atoms to which they are attached to form a ring in which R2R3 is represented by the structure
- R4, R5, R6 and R7 are each independently hydrogen, halogen, CN or NO2;
- and
- X is O or S,
- which process comprises reacting an N-[1-chloro-1-(perfluoroalkyl)methyl]arylimidoyl chloride compound having the formula II
- wherein A and n are as described above, with a dieneophile compound or a substituted haloethane compound, and a base, in the presence of a solvent, the dieneophile compound having the formula III and the substituted haloethane compound having the formula VI
- wherein W and Y are as described above, and Z is Cl, Br or I.
13 more elements
A process for the preparation of an arylpyrrole compound having the formula IX
- wherein
- Y is CN, NO2 or CO2R;
- R is C1-C4alkyl;
- n is an integer of 1, 2, 3, 4, 5, 6, 7 or 8;
- A is
- or
- L is hydrogen or halogen;
- M and Q are each independently hydrogen, halogen, CN, NO2, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkylsulfinyl, C1-C4haloalkylsulfinyl, C1-C4alkylsulfonyl or C1-C4haloalkylsulfonyl, or when M and Q are on adjacent positions they may be taken together with the carbon atoms to which they are attached to form a ring in which MQ represents the structure —OCH2O—, —OCF2O— or —CH═CH—CH═CH—;
- R1, R2 and R3 are each independently hydrogen, halogen, NO2 or CHO, or R2 and R3 may be taken together with the atoms to which they are attached to form a ring in which R2R3 is represented by the structure
- R4, R5, R6 and R7 are each independently hydrogen, halogen, CN or NO2;
- X is O or S;
- Hal is a halogen atom;
- and
- J is hydrogen or C1-C6alkoxymethyl, which process comprises:
- (a) reacting an N-[1-chloro-1-(perfluoroalkyl)methyl]arylimidoyl chloride compound having the formula II
- wherein A and n are as described above, with a dieneophile compound or a substituted haloethane compound, and a base, in the presence of a solvent, the dieneophile compound having the formula X and the substituted haloethane compound having the formula XII
- wherein Y is as described above, and Z is Cl, Br or I, to form a 2-aryl-5-(perfluoroalkyl)pyrrole compound having the formula XI
- (b) halogenating the formula XI compound to form the arylpyrrole compound of formula IX wherein J is hydrogen;
- and
- (c) optionally alkoxymethylating the formula IX compound.
17 more elements
Dependencies are inferred from the claim text.