IP Library Granted Patent US 7,528,260
Granted Patent B2
US 7,528,260 · App. 11/666,920 · Granted May 5, 2009

Method for preparing

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Quick Facts
Patent No.
US 7,528,260
App. No.
11/666,920
Granted
May 5, 2009
Kind
B2
Abstract

A method is disclosed for preparing compounds of Formula 1 by combining compounds of Formulae 2 and 3 and a sulfonyl chloride. Also disclosed are compounds of Formula 3, which are useful as starting materials for this method.

Claims (41)

1. A method for preparing a compound of Formula 1,

wherein

R 1 is CH 3 or Cl;

R 2 is Br, Cl, I or CN;

R 3 is H or C 1 -C 4 alkyl;

R 4 is Cl, Br, CF 3 , OCF 2 H or OCH 2 CF 3 ;

R 5 is F, Cl or Br;

R 6 is H, F or Cl;

Z is CR 7 or N; and

R 7 is H, F, Cl or Br; comprising:

combining (1) a carboxylic acid compound of Formula 2,

(2) an aniline compound of Formula 3,

and (3) a sulfonyl chloride to form the compound of Formula 1.

2. The method of claim 1 wherein the sulfonyl chloride is of Formula 4

R 8 S(O) 2 Cl  4

wherein R 8 is C 1 -C 4 alkyl, C 1 -C 2 haloalkyl, or phenyl optionally substituted with 1-3 substituents selected from the group consisting of halogen, C 1 -C 3 alkyl and nitro.

3. The method of claim 2 wherein the sulfonyl chloride is methanesulfonyl chloride.

4. The method of claim 1 wherein the carboxylic acid of Formula 2 is combined with the aniline of Formula 3 to form a mixture, and then the mixture is combined with the sulfonyl chloride.

5. The method of claim 4 wherein a base is combined with the compounds of Formulae 2 and 3 to form the mixture before combining with the sulfonyl chloride.

6. The method of claim 5 wherein the base is selected from tertiary amines.

7. The method of claim 6 wherein the base is selected from optionally substituted pyridines.

8. The method of claim 7 wherein the base is selected from 2-picoline, 3-picoline, 2,6-lutidine and pyridine.

9. The method of claim 8 wherein the sulfonyl chloride is of Formula 4

R 8 S(O) 2 Cl  4

wherein R 8 is C 1 -C 4 alkyl, C 1 -C 2 haloalkyl, or phenyl optionally substituted with 1-3 substituents selected from the group consisting of halogen, C 1 -C 3 alkyl and nitro.

10. The method of claim 1 or claim 4 wherein a solvent is combined with the compounds of Formulae 2 and 3 and the sulfonyl chloride.

11. The method of claim 10 wherein the solvent is acetonitrile.

12. A compound of Formula 3

wherein

R 1 is CH 3 or Cl;

R 2 is Br, Cl, I or CN; and

R 3 is H or C 1 -C 4 alkyl;

provided that

(a) when R 1 and R 2 are Cl, then R 3 is other than H, CH 2 CH 3 , or CH(CH 3 )CH 2 CH 3 ;

(b) when R 1 is CH 3 and R 2 is Cl, Br or CN, then R 3 is other than CH 3 or CH(CH 3 ) 2 ;

(c) when R 1 is Cl and R 2 is Cl or Br, then R 3 is other than H, CH 3 or CH(CH 3 ) 2 ; and

(d) when R 1 is CH 3 and R 2 is CN, then R 3 is other than H.

13. A compound of claim 12 wherein R 1 is CH 3.

14. A compound of claim 13 wherein R 2 is Cl and R 3 is H.

15. A compound of claim 13 wherein R 2 is CN and R 3 is CH 2 CH 3 , CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 3 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )CH 2 CH 3 or C(CH 3 ) 3 .

16. A compound of claim 12 wherein R 2 is CN.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 17, 2018
From: E.I. DU PONT DE NEMOURS AND COMPANY
To: FMC CORPORATION
Reel/Frame 046732/0016 →