Processes for the preparation of pesticidal compounds

• US 9,988,356 B2
• Filed: 09/26/2017
• Issued: 06/05/2018
• Est. Priority Date: 10/17/2013
• Status: Expired due to Fees

• Current Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Yang, Qiang, Lorsbach, Beth, Whiteker, Gregory, Roth, Gary, DeAmicis, Carl, Clark, Thomas, Gray, Kaitlyn, Canturk, Belgin, Kane, Elisabeth J., Zhang, Yu, Muhuhi, Joseck M.
• Primary Examiner(s): Morris, Patricia L
• Application Number:
  US15/715,813
• Publication Number:
  US 20180016238A1
• Time in Patent Office: 252 Days
• Field of Search: 5462754
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles
• CPC Class Codes: C07C 2601/02 with a three-membered ring
• CPC Class Codes: C07C 321/14 of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 321/16 of a saturated carbon skeleton containing rings
• CPC Class Codes: C07D 231/38 Nitrogen atoms nitro radicals C07D231/16
• CPC Class Codes: C07D 231/40 Acylated on said nitrogen atom
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond

Abstract

The present application provides processes for making pesticidal compounds and compounds useful both as pesticides and in the making of pesticidal compounds.

Claims

1. A process for the preparation of 3-chloro-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-amine (1d)

2. The process of claim 1, wherein the base in step (a) is sodium hydride (NaH), sodium tert-butoxide (NaOt-Bu), potassium tert-butoxide (KOt-Bu), or potassium tert-amyloxide.

3. The process of claim 1, wherein step (a) is carried out in a polar aprotic solvent.

4. The process of claim 3, wherein the polar aprotic solvent is tetrahydrofuran.

5. The process of claim 1, wherein step (a) is carried out at a temperature from about 20°

C. to about 40°

C.

6. The process of claim 1, wherein step (a) is carried out in the presence of an additive selected from potassium iodide (KI) or tetrabutylammonium iodide (TBAI).

7. The process of claim 1, wherein step (a) is carried out at a temperature from about 50°

C. to about 70°

C.

8. The process of claim 1, wherein step (a) is carried out in a sealed reactor at a temperature from about 50°

C. to about 70°

C.

9. The process of claim 1, wherein the base in step (a) is sodium hydride (NaH).

10. The process of claim 1, wherein the base in step (a) is sodium tert-butoxide (NaOt-Bu).

11. The process of claim 1, wherein the base in step (a) is potassium tert-butoxide (KOt-Bu).

12. The process of claim 1, wherein the base in step (a) is potassium tert-amyloxide.

13. The process of claim 1, wherein the base in step (a) is sodium tert-butoxide (NaOt-Bu) in tetrahydrofuran.

14. The process of claim 1, wherein the base in step (a) is sodium tert-butoxide (NaOt-Bu) in tetrahydrofuran in the presence of tetrabutylammonium iodide.