N′-({[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]acetyl}oxy)benzenecarboximidamide as an antimicrobial compound

1. A N′-({[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]acetyl}oxy)benzenecarboximidamide compound having the formula I:

2. The N′-({[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]acetyl}oxy)benzenecarboximidamide compound of claim 1 , wherein the compound is obtained as crystals.

3. A pharmaceutically acceptable composition comprising a therapeutically effective amount of the N′-({[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]acetyl}oxy)benzenecarboximidamide compound of claim 1 and a pharmaceutically acceptable carrier.

4. A method of treating a microbial infection in a patient comprising administering to a patient in need thereof a therapeutically effective amount of the N′-({[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]acetyl}oxy)benzenecarboximidamide compound of claim 1 ; wherein the microbial infection is caused by one or more bacteria or fungi.

5. The method of treating the microbial infection of claim 4 , wherein the microbial infection is caused by one or more gram positive bacteria, one or more gram negative bacteria, one or more fungi, or a combination thereof.

6. The method of treating the microbial infection of claim 5 , wherein the one or more gram positive bacteria are Bacillus cereus, Staphylococcus aureus , or a combination thereof.

7. The method of treating the microbial infection of claim 5 , wherein the one or more gram negative bacteria are Pseudomonas aeruginosa, Escherichia coli , or a combination thereof.

8. The method of treating the microbial infection of claim 5 , wherein the one or more fungi are Aspergillus flavus, Chrysosporium keratinophilum , or a combination thereof.

9. A method of making the N′-({[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]acetyl}oxy)benzenecarboximidamide compound of claim 1 , 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 N′-hydroxybenzenecarboximidamide 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′-({[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]acetyl}oxy)benzenecarboximidamide compound.

10. The method of making the N′-({[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]acetyl}oxy)benzenecarboximidamide compound of claim 9 , wherein the stirring the first reaction mixture lasts for at least minutes.

11. The method of making the N′-({[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]acetyl}oxy)benzenecarboximidamide compound of claim 9 , wherein the first reaction mixture is stirred at room temperature.

12. The method of making the N′-({[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]acetyl}oxy)benzenecarboximidamide compound of claim 9 , wherein the second reaction mixture is stirred for at least 6 hours.

13. The method of making the N′-({[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]acetyl}oxy)benzenecarboximidamide compound of claim 9 , wherein the formed precipitate is washed with cold acetonitrile.

14. The method of making the N′-({[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]acetyl}oxy)benzenecarboximidamide of claim 9 , wherein the 2-(5-phenyl-1,3,4-oxadiazol-2-ylthio)acetic acid and CDI are added in 2:2.4 molar ratio.

15. The method of making the N′-({[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]acetyl}oxy)benzenecarboximidamide compound of claim 9 , wherein the 2-(5-phenyl-1,3,4-oxadiazol-2-ylthio)acetic acid, CDI, and N′-hydroxybenzenecarboximidamide are added in a 2:2.4:2 molar ratio.

16. The method of making the N′-({[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]acetyl}oxy)benzenecarboximidamide compound of claim 9 , wherein the N′-({[(5-phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]acetyl}oxy)benzenecarboximidamide compound is obtained in a yield of 0%.