# US 12,180,204 B1 · 2-(benzo[d]thiazol-2-yl)-N′-(2-(5-phenyl-1,3,4-oxadiazol-2-ylthio)acetoxy)acetimidamide as an antimicrobial compound

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- Number: US 12,180,204 B1
- Document ID: US12180204B1
- Status: Granted
- Kind: B1
- Application number: 18/616,603
- Filed: 2024-03-26
- Granted: 2024-12-31
- Earliest claimed: 2023-10-13
- Assignees: King Faisal University
- Applicants: King Faisal University
- Inventors: Hany Mohamed Abd El-Lateef Ahmed; Mai Mostafa Khalaf Ali; Antar Ahmed Abdelhamid Ahmed; Amer A. Amer
- Web page: https://patentgrep.com/patent/US12180204B1

## CPC

- C07D 417/12: linked by a chain containing hetero atoms as chain links
- A61P 31/04: Antibacterial agents
- A61P 31/10: Antimycotics
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A 2-(benzol[d]thiazol-2-yl)-N′-(2-(5-phenyl-1,3,4-oxadiazol-2-ylthio)acetoxy)acetimidamide compound, its synthesis, and its use as an antimicrobial agent.

## Claims

### Claim 1

A method of making a 2-(benzo[d]thiazol-2-yl)-N′-(2-(5-phenyl-1,3,4-oxadiazol-2-ylthio)acetoxy)acetimidamide compound, the method comprising:
adding carbonyldiimidazole (CDI) to a solution of 2-(5-phenyl-1,3,4-oxadiazol-2-ylthio)acetic acid in acetonitrile to obtain a first reaction mixture;
stirring the first reaction mixture;
adding 2-(benzo[d]thiazol-2-yl)-N′-hydroxyacetimidamide to the first reaction mixture to obtain a second reaction mixture;
stirring the second reaction mixture; purifying a formed precipitate by filtering and recrystallization from acetonitrile; and
obtaining the 2-(benzo[d]thiazol-2-yl)-N′-(2-(5-phenyl-1,3,4-oxadiazol-2-ylthio)acetoxy)acetimidamide compound.

### Claim 2 (depends on 1)

The method of making the 2-(benzo[d]thiazol-2-yl)-N′-(2-(5-phenyl-1,3,4-oxadiazol-2-ylthio)acetoxy)acetimidamide compound of claim 1, wherein the stirring the first reaction mixture lasts for at least about 30 minutes.

### Claim 3 (depends on 1)

The method of making the 2-(benzo[d]thiazol-2-yl)-N′-(2-(5-phenyl-1,3,4-oxadiazol-2-ylthio)acetoxy)acetimidamide compound of claim 1, wherein the first reaction mixture is stirred at room temperature.

### Claim 4 (depends on 1)

The method of making the 2-(benzo[d]thiazol-2-yl)-N′-(2-(5-phenyl-1,3,4-oxadiazol-2-ylthio)acetoxy)acetimidamide compound of claim 1, wherein the second reaction mixture is stirred for at least about 6 hours.

### Claim 5 (depends on 1)

The method of making the 2-(benzo[d]thiazol-2-yl)-N′-(2-(5-phenyl-1,3,4-oxadiazol-2-ylthio)acetoxy)acetimidamide compound of claim 1, wherein the formed precipitate is washed with cold acetonitrile.

### Claim 6 (depends on 1)

The method of making the 2-(benzo[d]thiazol-2-yl)-N′-(2-(5-phenyl-1,3,4-oxadiazol-2-ylthio)acetoxy)acetimidamide of claim 1, wherein the 2-(5-phenyl-1,3,4-oxadiazol-2-ylthio)acetic acid and CDI are added in about a 2:2.4 molar ratio.

### Claim 7 (depends on 1)

The method of making the 2-(benzo[d]thiazol-2-yl)-N′-(2-(5-phenyl-1,3,4-oxadiazol-2-ylthio)acetoxy)acetimidamide compound of claim 1, wherein the 2-(5-phenyl-1,3,4-oxadiazol-2-ylthio)acetic acid, CDI, and 2-(benzo[d]thiazol-2-yl)-N′-hydroxyacetimidamide are added in about a 2:2.4:2 molar ratio.