4-chloro-n'-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)benzimidamide as an antimicrobial compound
A 4-chloro-N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)benzimidamide compound, its synthesis, and its use as an antimicrobial agent.
1. A method of making a 4-chloro-N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)benzimidamide compound; the method comprising:
adding carbonyldiimidazole (CDI) to a solution of 2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetic acid in acetonitrile to obtain a reaction mixture;
adding 4-chloro-N-hydroxybenzene-1-carboximidamide to the reaction mixture with stirring until reaction completion to obtain a precipitate; and
obtaining the 4-chloro-N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)benzimidamide compound.
2. The method of making the 4-chloro-N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)benzimidamide compound of claim 1 , wherein the reaction mixture is stirred at room temperature for at least about 30 minutes before the adding of the 4-chloro-N′-hydroxybenzene-1-carboximidamide.
3. The method of making the 4-chloro-N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)benzimidamide of claim 1 , wherein after the adding of the 4-chloro-N′-hydroxybenzene-1-carboximidamide the reaction mixture is stirred for at least about 6 hours.
4. The method of making the 4-chloro-N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)benzimidamide compound of claim 1 , wherein the precipitate is collected by filtration, washed several times with cold acetonitrile, dried, and recrystallized from the acetonitrile to obtain the 4-chloro-N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)benzimidamide compound.
5. The method of making the 4-chloro-N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)benzimidamide compound of claim 1 , wherein the 2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetic acid and 4-chloro-N′-hydroxybenzene-1-carboximidamide are added in an about 1:1 molar ratio.
6. The method of making the 4-chloro-N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)benzimidamide compound of claim 1 , wherein the 2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetic acid and CDI are added in an about 1:1.2 molar ratio.
7. The method of making the 4-chloro-N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)benzimidamide compound of claim 1 , wherein the 4-chloro-N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)benzimidamide compound is obtained in an about 73% yield.