Processes for the preparation of pesticidal compounds

Patent metadata

Field	Value
Publication number	US-9988356-B2
Application number	US-201715715813-A
Country	US
Kind code	B2
Filing date	Sep 26, 2017
Priority date	Oct 17, 2013
Publication date	Jun 5, 2018
Grant date	Jun 5, 2018

Abstract

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

First claim

What is claimed is:

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

which comprises:
(a) alkylating N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)acetamide (1c)

with ethyl bromide in the presence of a base to produce N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethylacetamide (1c′)

and
(b) reacting (1c′) with hydrochloric acid in water at temperatures between about 70° C. and about 90° C.

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.

Assignees

• Dow Agrosciences Llc

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

Classifications

• A01N43/56 Primary

  1,2-Diazoles; Hydrogenated 1,2-diazoles · CPC title

• C07D401/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D231/38 Primary

  Nitrogen atoms (nitro radicals C07D231/16) · CPC title

• C07C2601/02

  with a three-membered ring · CPC title

• Y10S424/10

  Insect repellent · CPC title