Composition and method for preparing N-phenylpyrazole-1-carboxamides
An improved method is disclosed for preparing an organic pesticide of Formula 4-A from (1) a composition comprising: (a) a crystalline organic pesticide; (b and c) compounds of Formulae 1 and 2; (d) an amine base and (e) an aprotic solvent; (2) reacting with a sulfonyl chloride of Formula 3; and (3) allowing the mixture to proceed to an organic pesticide of Formula 4-A. wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are as defined in the disclosure.
1 . A composition comprising:
(a) a crystalline organic pesticide, wherein the crystalline organic pesticide is a crystalline compound of Formula 4,
wherein
R 1 is CH 3 ;
R 2 is CN;
R 3 is CH 3 ;
R 4 is Br;
R 5 is Cl;
R 6 is H; and
Z is N;
(b) a carboxylic acid compound of Formula 1,
wherein
R 4 is Br;
R 5 is Cl;
R 6 is H; and
Z is N;
(c) an aniline compound of Formula 2,
wherein
R 1 is CH 3 ;
R 2 is CN;
R 3 is CH 3 ;
(d) an amine base and
(e) an aprotic solvent,
wherein the amount of crystalline compound of Formula 4 is 5 mol % to 30 mol % per mol of the carboxylic acid compound of Formula 1.
2 . The composition of claim 1 wherein the amine base is selected from optionally substituted pyridines.
3 . The composition of claim 1 wherein the amine base is 3-picoline.
4 . The composition of claim 1 wherein the aprotic solvent is acetonitrile.
5 . The composition of claim 1 wherein the amount of crystalline compound of Formula 4 is 10 mol % to 25 mol % per mol of the carboxylic acid compound of Formula 1.
6 . The method to prepare a compound of Formula 4-A,
wherein
R 1 is CH 3 ;
R 2 is CN;
R 3 is CH 3 ;
R 4 is Br;
R 5 is Cl;
R 6 is H; and
Z is N;
the method comprising the steps of:
(1) forming the composition of claim 1 ;
(2) reacting the composition of claim 1 with a sulfonyl chloride compound of Formula 3,
R 8 S(O) 2 Cl 3
wherein
R 8 is carbon-based radical; and
(3) allowing the coupling of the acid activated mixture to proceed for the formation of a compound of Formula 4-A.
7 . The method of claim 6 wherein the sulfonyl chloride compound of Formula 3 is methanesulfonyl chloride.
8 . The method of claim 6 further comprising the step of:
(4) adding water to the reaction.
9 . The composition of claim 1 wherein the amount of the aprotic solvent is at least 600 mL aprotic solvent per mol of the carboxylic acid compound of Formula 1.
10 . The composition of claim 1 wherein the amount of the aprotic solvent is between 1800 to 600 mL aprotic solvent per mol of the carboxylic acid compound of Formula 1.
11 . The composition of claim 1 wherein the amount of the aprotic solvent is between 1200 to 600 mL aprotic solvent per mol of the carboxylic acid compound of Formula 1.