Methods of coupling a carbon containing moiety to an amine containing moiety

Patent metadata

Field	Value
Publication number	US-11787770-B2
Application number	US-202117323290-A
Country	US
Kind code	B2
Filing date	May 18, 2021
Priority date	May 19, 2020
Publication date	Oct 17, 2023
Grant date	Oct 17, 2023

Abstract

The invention generally relates to methods of coupling a carbon containing moiety to an amine containing moiety.

First claim

What is claimed is:

1. A method of coupling a carbon containing moiety to an amine containing moiety, the method comprising: generating a microdroplet comprising a carbon containing moiety and an amine containing moiety, wherein the microdroplet comprises an acidic surface that facilitates a reaction between the carbon containing moiety and the amine containing moiety and generates a reaction product comprising a carbon-nitrogen bond via the amine of the amine containing moiety; wherein the carbon containing moiety is an aromatic-1,2-diamine that is at least one selected from the group consisting of: 1,2-phenyldiamine (PDA), 4-methyl-1,2-phenyldiamine, 4,5-dimethyl-1,2-phenyldiamine, 4-nitro-1,2-phenyldiamine, 4-chloro-1,2-phenyldiamine, 4-methoxy-1.2-phenyldiamine, 1,2-diaminonapthalene); and the carboxylic acid is at least one selected from the group consisting of: (formic acid (FA), acetic acid (AA), trifluoroacetic acid (TFAA), propanoic acid (PA) and benzoic acid (BA)).

2. The method of claim 1 , wherein generating the microdroplet is by use of an electrospray probe or nano-electrospray probe.

3. The method of claim 1 , wherein the microdroplet generates an environment that accelerates a rate of the reaction as compared to the same reaction occurring outside of a microdroplet environment.

4. The method of claim 1 , wherein the method further comprises analyzing the reaction product in a mass spectrometer by directing the microdroplets into the mass spectrometer.

5. The method of claim 1 , wherein the method further comprises collecting the reaction product by directing the microdroplets onto a surface.

6. The method of claim 1 , wherein the method is conducted without use of a metal or metal catalyst.

7. The method of claim 6 , wherein the method is conducted without use of a base.

8. The method of claim 1 , wherein the reaction product is a benzimidazole.

9. A method of producing a benzimidazole, the method comprising: generating a microdroplet comprising a carboxylic acid and an aromatic-1,2-diamine, wherein the microdroplet comprises an acidic surface that facilitates a reaction between the carboxylic acid and the aromatic-1,2-diamine and generates a benzimidazole, wherein: the aromatic-1,2-diamine is at least one selected from the group consisting of: 1,2-phenyldiamine (PDA), 4-methyl-1,2-phenyldiamine, 4,5-dimethyl-1,2-phenyldiamine, 4-nitro-1,2-phenyldiamine, 4-chloro-1,2-phenyldiamine, 4-methoxy-1.2-phenyldiamine, 1,2-diaminonapthalene); and the carboxylic acid is at least one selected from the group consisting of: (formic acid (FA), acetic acid (AA), trifluoroacetic acid (TFAA), propanoic acid (PA) and benzoic acid (BA)).

10. The method of claim 9 , wherein generating the microdroplets is by use of an electrospray probe or nano-electrospray probe.

11. The method of claim 9 , wherein microdroplet generates an environment that accelerates a rate of the reaction as compared to the same reaction occurring outside of a microdroplet environment.

12. The method of claim 1 , wherein the method further comprises analyzing the benzimidazole in a mass spectrometer by directing the microdroplets into the mass spectrometer.

13. The method of claim 9 , wherein the method further comprises collecting the benzimidazole by directing the microdroplets onto a surface.

14. The method of claim 1 , wherein the method is conducted without use of a metal or metal catalyst.

15. The method of claim 14 , wherein the method is conducted without use of a base.

16. The method of claim 9 , wherein there is a 1:1 molar ratio of the aromatic-1,2-diamine and the carboxylic acid.

17. The method of claim 9 , wherein a solvent in the microdroplet is methanol.

Assignees

• Purdue Research Foundation

Inventors

• Cooks Robert Graham
• Basuri Pallab
• Morato Nicolás M
• Pradeep Thalappil

Classifications

• C07D235/08 Primary

  Radicals containing only hydrogen and carbon atoms · CPC title

• C07D235/02

  condensed with carbocyclic rings or ring systems · CPC title

• C07D235/06

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2 · CPC title

• C07D235/10

  Radicals substituted by halogen atoms or nitro radicals · CPC title