# US 11,999,712 B1 · 2-(benzo[b]thiophen-3-yl)-1-butyl-4,5-diphenyl-1H-imidazole as an anti-inflammatory and anti-microbial compound

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- Number: US 11,999,712 B1
- Document ID: US11999712B1
- Status: Granted
- Kind: B1
- Application number: 18/415,207
- Filed: 2024-01-17
- Granted: 2024-06-04
- Earliest claimed: 2023-09-05
- Assignees: King Faisal University
- Applicants: King Faisal University
- Inventors: Mai Mostafa Khalaf Ali; Hany Mohamed Abd El-Lateef Ahmed; Antar Ahmed Abdelhamid Ahmed; Adel A. Marzouk
- Web page: https://patentgrep.com/patent/US11999712B1

## CPC

- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- 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 compound 2-(Benzo[b]thiophen-3-yl)-1-butyl-4,5-diphenyl-1H-imidazole compound, its synthesis, and its use as an anti-microbial and anti-inflammatory agent.

## Claims

### Claim 1

A method of making a 2-(Benzo[b]thiophen-3-yl)-1-butyl-4,5-diphenyl-1H-imidazole compound, the method comprising:
adding benzil, 1-benzothiophene-3-carbaldehyde, ammonium acetate, and n-butylamine to piperidinium hydrogen sulfate in an oil bath to obtain a reaction mixture;
heating the reaction mixture with stirring until reaction completion to obtain a crude product;
purifying the crude product by recrystallization using absolute ethyl alcohol; and
obtaining the 2-(Benzo[b]thiophen-3-yl)-1-butyl-4,5-diphenyl-1H-imidazole compound.

### Claim 2 (depends on 1)

The method of making the 2-(Benzo[b]thiophen-3-yl)-1-butyl-4,5-diphenyl-1H-imidazole compound of claim 1, wherein the oil bath is at a temperature of about 30° C.

### Claim 3 (depends on 1)

The method of making the 2-(Benzo[b]thiophen-3-yl)-1-butyl-4,5-diphenyl-1H-imidazole compound of claim 1, wherein heating is at a temperature of about 105° C.

### Claim 4 (depends on 1)

The method of making the 2-(Benzo[b]thiophen-3-yl)-1-butyl-4,5-diphenyl-1H-imidazole compound of claim 1, wherein after reaction completion the reaction mixture is washed with water.

### Claim 5 (depends on 1)

The method of making the 2-(Benzo[b]thiophen-3-yl)-1-butyl-4,5-diphenyl-1H-imidazole compound of claim 1, wherein the benzil, the 1-benzothiophene-3-carbaldehyde, and the ammonium acetate are added in an about 1:1:1 molar ratio.

### Claim 6 (depends on 1)

The method of making the 2-(Benzo[b]thiophen-3-yl)-1-butyl-4,5-diphenyl-1H-imidazole compound of claim 1, wherein the benzil, the 1-benzothiophene-3-carbaldehyde, the ammonium acetate, and the n-butylamine are added in an about 1:1:1:0.5 molar ratio.

### Claim 7 (depends on 1)

The method of making the 2-(Benzo[b]thiophen-3-yl)-1-butyl-4,5-diphenyl-1H-imidazole compound of claim 1, wherein the 2-(Benzo[b]thiophen-3-yl)-1-butyl-4,5-diphenyl-1H-imidazole compound is obtained in an about 95% yield.