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- Nachgewiesen in: USPTO Patent Grants
- Sprachen: English
- Patent Number: 11840,545
- Publication Date: December 12, 2023
- Appl. No: 18/222277
- Application Filed: July 14, 2023
- Assignees: KING FAISAL UNIVERSITY (Al-Ahsa, SA)
- Claim: 1. A compound of the formula I: [chemical expression included] wherein X 1 , X 2 , and X 3 are each independently selected from the group consisting of chlorine, hydrogen, NO 2 , and bromine.
- Claim: 2. The compound of claim 1 , wherein X 1 and X 3 are both either hydrogen or chlorine.
- Claim: 3. The compound of claim 1 , wherein when X 1 and X 3 are both hydrogen, X 2 is bromine or NO 2 and when X 1 and X 3 are both chlorine, X 2 is hydrogen.
- Claim: 4. The compound of claim 1 , wherein the compound is selected from the group consisting of: (3R,6'S,7′R)-6-chloro-7′-(2,4-dichlorophenyl)-6′-(5-methyl-1H-1,2,3-triazole-4-carbonyl)-1′,6′,7′,7a′-tetrahydro-3′H-spiro[indoline-3,5′-pyrrolo[1,2-c]thiazol]-2-one (SP34); (3R,6'S,7′R)-6-chloro-6′-(5-methyl-1H-1,2,3-triazole-4-carbonyl)-7′-(3-nitrophenyl)-1′,6′,7′,7a′-tetrahydro-3′H-spiro[indoline-3,5′-pyrrolo[1,2-c]thiazol]-2-one (SP37); and (3R,6'S,7′R)-7′-(3-bromophenyl)-6-chloro-6′-(5-methyl-1H-1,2,3-triazole-4-carbonyl)-1′,6′,7′,7a′-tetrahydro-3′H-spiro[indoline-3,5′-pyrrolo[1,2-c]thiazol]-2-one (SP311).
- Claim: 5. A copper complex comprising a complex of the formula II: CuL II wherein L is a ligand that is the compound of claim 1 .
- Claim: 6. A method for making the copper complex of claim 5 , the method comprising: reacting equimolar amounts of the compound of claim 1 and copper chloride (CuCl) in an organic solvent; and obtaining the copper complex.
- Claim: 7. An anticorrosion coating comprising the copper complex of claim 5 .
- Claim: 8. A method of preventing corrosion in a material, comprising: administering a continuous monolayer of the anticorrosion coating of claim 7 to a material selected from the group consisting of steel, iron, copper, and a combination thereof.
- Claim: 9. The method of claim 8 , wherein the material is formed as a homogeneous flat solid surface.
- Claim: 10. The method of claim 8 , wherein the material is formed as an electrical wire, a pipe, or piping.
- Claim: 11. A method of preparing the compound of claim 1 , the method comprising: adding about one equivalent of (s)-Thiazolidine-4-carboxylic acid to a solution of about one equivalent of a compound of formula III in an organic solvent to obtain a first mixture: [chemical expression included] wherein R 1 is selected from the group consisting of hydrogen, chlorine, fluorine, bromine, and NO 2 and R 2 is selected from the group consisting of hydrogen and chlorine; adding a chalcone of formula IV to the first mixture and refluxing for about 6 to about 12 hours to obtain a second mixture: [chemical expression included] wherein X 1 , X 2 , and X 3 are each independently selected from the group consisting of chlorine, hydrogen, NO 2 , and bromine; evaporating the organic solvent from the second mixture to obtain a crude product; and purifying the crude product by column chromatography to obtain the compound of claim 1 .
- Claim: 12. The method of claim 11 , wherein the organic solvent is methanol.
- Claim: 13. The method of claim 11 , wherein a yield of the compound of claim 1 is about 65% to about 90%.
- Claim: 14. A method of preparing the compound of claim 1 , the method comprising: adding about one equivalent of 1-(1-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-5-methyl-1H-1,2,3-triazol-4-yl) (B) to ethanol until dissolved; adding an about 7% KOH dropwise with stirring for about 5 minutes to obtain a reaction mixture; placing the reaction mixture in an ice bath and adding a benzaldehyde of formula V with stirring for about 1 to about 2 hours: [chemical expression included] wherein X 1 , X 2 , and X 3 are each independently selected from the group consisting of chlorine, hydrogen, NO 2 , and bromine; evaporating the ethanol and extracting a chalcone of formula IV: [chemical expression included] adding one equivalent of (s)-Thiazolidine-4-carboxylic acid to a solution of one equivalent of a compound of formula III in an organic solvent to obtain a first mixture: [chemical expression included] wherein R 1 is selected from the group consisting of hydrogen, chlorine, fluorine, bromine, and NO 2 and R 2 is selected from the group consisting of hydrogen and chlorine; adding the chalcone of formula IV to the first mixture and refluxing for about 6 to about 12 hours to obtain a second mixture; evaporating the organic solvent from the second mixture to obtain a crude product; and purifying the crude product by column chromatography to obtain the compound of claim 1 .
- Claim: 15. A method of preparing the compound of claim 1 , the method comprising: adding methanol to cyanuric chloride followed by NaHCO 3 with stirring at about 0° C., followed by stirring at room temperature for about 30 minutes, extraction, and drying to obtain 2,4-dichloro-6-methoxy-1,3,5-triazine; dissolving the 2,4-dichloro-6-methoxy-1,3,5-triazine in MeCn followed by adding a solution of sodium azide in water and stirring, first in an ice bath then at room temperature, extraction, concentration, and drying to obtain 2-Azido-4,6-dimethoxy-1,3,5-triazine (A); adding about one equivalent of the 2-Azido-4,6-dimethoxy-1,3,5-triazine (A) to a stirred solution of about 1.2 equivalents of acetylacetone and about 1.2 equivalents of TEA in DMF followed by adding water, filtering, and drying to obtain 1-(1-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-5-methyl-1H-1,2,3-triazol-4-yl) (B); adding about one equivalent of the 1-(1-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-5-methyl-1H-1,2,3-triazol-4-yl) (B) to ethanol until dissolved; adding an about 7% KOH dropwise with stirring for about 5 minutes to obtain a reaction mixture; placing the reaction mixture in an ice bath and adding a benzaldehyde of formula V with stirring for about 1 to about 2 hours: [chemical expression included] wherein X 1 , X 2 , and X 3 are each independently selected from the group consisting of chlorine, hydrogen, NO 2 , and bromine; evaporating the ethanol and extracting a chalcone of formula IV: [chemical expression included] adding one equivalent of (s)-Thiazolidine-4-carboxylic acid to a solution of one equivalent of a compound of formula III in an organic solvent to obtain a first mixture: [chemical expression included] wherein R 1 is selected from the group consisting of hydrogen, chlorine, fluorine, bromine, and NO 2 and R 2 is selected from the group consisting of hydrogen and chlorine; adding the chalcone of formula IV to the first mixture and refluxing for about 6 to about 12 hours to obtain a second mixture; evaporating the organic solvent from the second mixture to obtain a crude product; and purifying the crude product by column chromatography to obtain the compound of claim 1 .
- Claim: 16. The method of claim 15 , wherein a yield of the compound of claim 1 is about 65% to about 90%.
- Patent References Cited: 8742109 June 2014 Cadieux et al. ; 8916580 December 2014 Chafeev ; 2777543 April 2011
- Other References: Altowyan et al., “[3+2] Cycloaddition Reaction for the Stereoselective Synthesis of a New Spirooxindole Compound Grafted Imidazo[2,1-b]thiazole Scaffold: Crystal Structure and Computational Study”, Crystals 2022, 12(1), 5. cited by applicant ; Kumar et al., “Sustainable synthesis of highly diastereoselective & fluorescent active spirooxindoles catalyzed by copper oxide nanoparticle immobilized on microcrystalline cellulose”, Applied Organometallic Chemistry, vol. 36, Issue 7, Jul. 2022. cited by applicant
- Primary Examiner: Kosack, Joseph R
- Attorney, Agent or Firm: Nath, Goldberg & Meyer ; Litman, Richard C.
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