# US 12,180,171 B1 · N′-(2-naphthoyloxy)-2-(benzo[d]oxazol-2-yl)acetimidamide as an antimicrobial compound

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- Number: US 12,180,171 B1
- Document ID: US12180171B1
- Status: Granted
- Kind: B1
- Application number: 18/414,737
- Filed: 2024-01-17
- Granted: 2024-12-31
- Earliest claimed: 2023-10-13
- Assignees: King Faisal University Al-Ahsa, Saudia Arabia
- 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/US12180171B1

## CPC

- C07D 263/56: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- A61P 31/04: Antibacterial agents
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

A N′-(2-naphthoyloxy)-2-(benzo[d]oxazol-2-yl)acetimidamide compound, its synthesis, and its use as an antimicrobial agent.

## Claims

### Claim 1

A method of making a N′-(2-naphthoyloxy)-2-(benzo[d]oxazol-2-yl)acetimidamide compound, the method comprising:
adding carbonyldiimidazole (CDI) to a solution of 2-naphthoic acid in acetonitrile to obtain a first reaction mixture;
stirring the first reaction mixture;
adding N′-hydroxy-2-(1,3-benzoxazol-2-yl)-ethyl-carboximidamide 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 N′-(2-naphthoyloxy)-2-(benzo[d]oxazol-2-yl)acetimidamide compound.

### Claim 2 (depends on 1)

The method of making the N′-(2-naphthoyloxy)-2-(benzo[d]oxazol-2-yl)acetimidamide compound of claim 1, wherein the stirring the first reaction mixture lasts for about 35 minutes.

### Claim 3 (depends on 1)

The method of making the N′-(2-naphthoyloxy)-2-(benzo[d]oxazol-2-yl)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 N′-(2-naphthoyloxy)-2-(benzo[d]oxazol-2-yl)acetimidamide compound of claim 1, wherein the second reaction mixture is stirred for about 4 hours.

### Claim 5 (depends on 1)

The method of making the N′-(2-naphthoyloxy)-2-(benzo[d]oxazol-2-yl)acetimidamide compound of claim 1, wherein the formed precipitate is washed with cold acetonitrile.

### Claim 6 (depends on 1)

The method of making the N′-(2-naphthoyloxy)-2-(benzo[d]oxazol-2-yl)acetimidamide compound of claim 1, wherein the 2-naphthoic acid and CDI are added in about a 2:2.4 molar ratio.

### Claim 7 (depends on 1)

The method of making the N′-(2-naphthoyloxy)-2-(benzo[d]oxazol-2-yl)acetimidamide compound of claim 1, wherein the 2-naphthoic acid, CDI, and N′-hydroxy-2-(1,3-benzoxazol-2-yl)-ethyl-carboximidamide are added in about a 2:2.4:2 molar ratio.