# US 11,999,704 B1 · 1-(2-hydroxybenzylideneamino)-5-phenylimidazolidine-2,4-dione as an antimicrobial compound

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- Number: US 11,999,704 B1
- Document ID: US11999704B1
- Status: Granted
- Kind: B1
- Application number: 18/430,527
- Filed: 2024-02-01
- Granted: 2024-06-04
- Earliest claimed: 2023-10-23
- Assignees: King Faisal University
- Applicants: King Faisal University
- Inventors: Mai Mostafa Khalaf Ali; Hany Mohamed Abd El-Lateef Ahmed; Antar Ahmed Abdelhamid Ahmed; Amer A. Amer
- Web page: https://patentgrep.com/patent/US11999704B1

## CPC

- C07D 233/80: with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
- A61P 31/04: Antibacterial agents
- A61P 31/10: Antimycotics
- Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

A 1-(2-hydroxybenzylideneamino)-5-phenylimidazolidine-2,4-dione compound, its synthesis, and its use as an antimicrobial agent.

## Claims

### Claim 1

A method of making a 1-(2-hydroxybenzylideneamino)-5-phenylimidazolidine-2,4-dione compound, the method comprising:
adding a mixture of semicarbazide hydrochloride, salicylaldehyde, and sodium ethoxide to ethanol with stirring to obtain a first reaction mixture;
adding phenylglyoxal to the first reaction mixture to obtain a second reaction mixture;
stirring the second reaction with reflux followed by cooling to room temperature to obtain a solid;
purifying the solid by filtering and recrystallization using ethanol; and
obtaining the 1-(2-hydroxybenzylideneamino)-5-phenylimidazolidine-2,4-dione compound.

### Claim 2 (depends on 1)

The method of making the 1-(2-hydroxybenzylideneamino)-5-phenylimidazolidine-2,4-dione compound of claim 1, wherein the semicarbazide hydrochloride, salicylaldehyde, and sodium ethoxide are added in a 1:1:4 ratio.

### Claim 3 (depends on 1)

The method of making the 1-(2-hydroxybenzylideneamino)-5-phenylimidazolidine-2,4-dione compound of claim 1, wherein the semicarbazide hydrochloride, salicylaldehyde, sodium ethoxide, and phenylglyoxal are added in a 1:1:4:1 molar ratio.

### Claim 4 (depends on 1)

The method of making the 1-(2-hydroxybenzylideneamino)-5-phenylimidazolidine-2,4-dione compound of claim 1, wherein the first reaction mixture is stirred for at least about 2 hours.

### Claim 5 (depends on 1)

The method of making the 1-(2-hydroxybenzylideneamino)-5-phenylimidazolidine-2,4-dione compound of claim 1, wherein the stirring with reflux step lasts for at least about 4 hours.

### Claim 6 (depends on 1)

The method of making the 1-(2-hydroxybenzylideneamino)-5-phenylimidazolidine-2,4-dione compound of claim 1, wherein the compound 1-(2-hydroxybenzylideneamino)-5-phenylimidazolidine-2,4-dione is obtained in a yield of about 65%.

### Claim 7 (depends on 1)

The method of making the 1-(2-hydroxybenzylideneamino)-5-phenylimidazolidine-2,4-dione compound of claim 1, wherein the compound 1-(2-hydroxybenzylideneamino)-5-phenylimidazolidine-2,4-dione is obtained as a yellow solid.