Herbicidal compounds
US-9701662-B2 · Jul 11, 2017 · US
Process for the synthesis of intermediates useful for preparing 1,3,4-triazine derivatives
US10294196B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-10294196-B2 |
| Application number | US-201615777314-A |
| Country | US |
| Kind code | B2 |
| Filing date | Nov 14, 2016 |
| Priority date | Nov 18, 2015 |
| Publication date | May 21, 2019 |
| Grant date | May 21, 2019 |
How to read this patent
A practical reading order for non-experts. Skip the full description unless you need deep technical detail.
- Title
What the patent document calls the invention.
- Abstract
A short plain-language summary of the technical disclosure.
- Assignees and inventors
Who owns or filed the patent and who is credited as inventor.
- Key dates
Filing, priority, publication, and grant dates set the timeline.
- First independent claim
The legal scope of protection — read this for what is actually claimed.
- CPC / IPC classifications
Technology tags used to group this patent with similar filings.
- Citations and related patents
Prior art links and similar publications in this corpus.
Abstract
Official abstract text for this publication.
A process for the synthesis of 1,3-diethyl 2-(2-methylhydrazinylidene)propanedioate comprising the step of: reacting 2-halosubstituted diethyl malonate or mixtures of 2-halo-substituted diethyl malonates with methylhydrazine or the salt thereof in the presence of an acid catalyst is disclosed. 1,3-diethyl 2-(2-methylhydrazinylidene)propanedioate is an intermediate useful for preparing 1,3,4-triazines.
First claim
Opening claim text (preview).
What is claimed is: 1. A process for the preparation of 1,3-diethyl 2-(2-methylhydrazinylidene)propanedioate, comprising the step of: reacting 2-halosubstituted diethyl malonate with methylhydrazine or a salt thereof optionally in the presence of an acid catalyst. 2. The process according to claim 1 , wherein the 2-halo-substituted diethyl malonate is selected from the group consisting of diethyl-2-bromomalonate, diethyl-2,2-dibromomalonate, diethyl-2-chloromalonate, diethyl-2,2-dichloromalonate, and mixtures thereof. 3. The process according to claim 1 , wherein 2-halo-substituted diethyl malonate is a mixture selected from the group consisting of: diethyl-2-bromomalonate and diethyl 2,2-dibromomalonate; diethyl-2-chloromalonate and diethyl-2,2-dichloromalonate; diethyl-2-bromomalonate and diethyl-2-chloromalonate; diethyl-2-bromomalonate and diethyl-2,2-dichloromalonate; diethyl-2,2-dibromomalonate and diethyl-2-chloromalonate; diethyl-2,2-dibromomalonate and diethyl-2,2-dichloromalonate; diethyl-2-bromomalonate and diethyl-2,2-dibromomalonate and diethyl-2-chloromalonate; diethyl-2-bromomalonate and diethyl-2,2-dibromomalonate and diethyl-2,2-dichloromalonate; diethyl-2-bromomalonate and diethyl-2-chloromalonate and diethyl-2,2-dichloromalonate; diethyl-2,2-dibromomalonate and diethyl-2-chloromalonate and diethyl-2,2-dichloromalonate; diethyl-2-bromomalonate and diethyl-2,2-dibromomalonate and diethyl-2-chloromalonate and diethyl-2,2-dichloromalonate. 4. The process according to claim 1 , wherein the reacting step is carried out in a solvent selected from the group consisting of: methanol, ethanol, 1-propanol, isopropyl alcohol, acetonitrile and mixtures thereof. 5. The process according to claim 1 , wherein the reacting step is carried out in the presence of an acid catalyst selected from the group consisting of: acetic acid, hydrochloric acid, sulfuric acid, phosphoric acid, and mixtures thereof. 6. The process according to claim 1 , wherein the reacting step in carried out at the temperature range from 10 to 80° C. 7. A process for the preparation of 1,3-diethyl 2-(2-methylhydrazinylidene)propanedioate, comprising the step of: reacting 2-halo-substituted diethyl malonate with methylhydrazine or a salt thereof in a solvent selected from the group consisting of: methanol, ethanol, 1-propanol, isopropyl alcohol, acetonitrile and mixtures thereof, in the presence of a catalyst selected from the group consisting of acetic acid, hydrochloric acid, sulfuric acid, phosphoric acid and mixtures thereof, and at a temperature ranging from about 10 to about 80° C. 8. The process according to claim 7 , wherein the reacting step is carried out in ethanol in the presence of acetic acid at the temperature range of from 20 to 70° C. 9. The process according to claim 7 , wherein 2-halo-substituted diethyl malonate is a mixture selected from the group consisting of: diethyl-2-bromomalonate and diethyl 2,2-dibromomalonate; diethyl-2-chloromalonate and diethyl-2,2-dichloromalonate; diethyl-2-bromomalonate and diethyl-2-chloromalonate; diethyl-2-bromomalonate and diethyl-2,2-dichloromalonate; diethyl 2,2-dibromomalonate and diethyl 2-chloromalonate; diethyl-2,2-dibromomalonate and diethyl-2,2-dichloromalonate; diethyl-2-bromomalonate and diethyl-2,2-dibromomalonate and diethyl-2-chloromalonate; diethyl-2-bromomalonate and diethyl-2,2-dibromomalonate and diethyl-2,2-dichloromalonate; diethyl-2-bromomalonate and diethyl-2-chloromalonate and diethyl-2,2-dichloromalonate; diethyl-2,2-dibromomalonate and diethyl-2-chloromalonate and diethyl-2,2-dichloromalonate; diethyl-2-bromomalonate and diethyl-2,2-dibromomalonate and diethyl-2-chloromalonate and diethyl-2,2-dichloromalonate. 10. The process according to claim 7 , wherein the process is carried out by adding 2-halo-substituted diethyl malonate to methylhydrazine dropwise. 11. The process according to claim 1 , wherein the reacting step is carried out at the temperature range from 20 to 70° C. 12. The process according to claim 1 , wherein the reacting step is carried out in a solvent selected from the group consisting of: methanol, ethanol, 1-propanol, isopropyl alcohol, acetonitrile and mixtures thereof at the temperature range from 10 to 80° C. 13. The process according to claim 12 , wherein the reacting step is carried out in ethanol in the presence of acetic acid.
Assignees
Inventors
Classifications
to carbon atoms of a saturated carbon skeleton · CPC title
- C07C249/16Primary
of hydrazones · CPC title
Formation or introduction of functional groups containing nitrogen · CPC title
Patent family
Related publications grouped by family.
External sources
Frequently asked questions
Answers are generated from the same data shown on this page.
- What does patent US10294196B2 cover?
- A process for the synthesis of 1,3-diethyl 2-(2-methylhydrazinylidene)propanedioate comprising the step of: reacting 2-halosubstituted diethyl malonate or mixtures of 2-halo-substituted diethyl malonates with methylhydrazine or the salt thereof in the presence of an acid catalyst is disclosed. 1,3-diethyl 2-(2-methylhydrazinylidene)propanedioate is an intermediate useful for preparing 1,3,4-tri…
- Who is the assignee on this patent?
- Fmc Corp
- What technology area does this patent fall under?
- Primary CPC classification C07C249/16. Mapped technology areas include Chemistry & Metallurgy.
- When was this patent published?
- Publication date Tue May 21 2019 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
- What related patents are in patentsdb?
- We list 1 related publication on this page (citations in our corpus or others sharing the same primary CPC).