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

Patent metadata

Field	Value
Publication number	US-2024025861-A1
Application number	US-202318367032-A
Country	US
Kind code	A1
Filing date	Sep 12, 2023
Priority date	May 19, 2020
Publication date	Jan 25, 2024
Grant date	—

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.

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 carbon containing moiety comprises a carboxylic acid.

9 . The method of claim 8 , wherein the amine containing moiety comprises an aromatic-1,2-diamine.

10 . The method of claim 9 , wherein the reaction product is a benzimidazole.

11 . 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.

12 . The method of claim 11 , wherein generating the microdroplets is by use of an electrospray probe or nano-electrospray probe.

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

14 . 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.

15 . The method of claim 11 , wherein the method further comprises collecting the benzimidazole by directing the microdroplets onto a surface.

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

17 . The method of claim 16 , wherein the method is conducted without use of a base.

18 . The method of claim 11 , wherein there is a 1:1 molar ratio of the aromatic-1,2-diamine and the carboxylic acid.

19 . The method of claim 11 , wherein a solvent in the microdroplet is methanol.

20 . The method of claim 11 , 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)).

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