Process of making 3-phenylimino-3H-phenothiazine
View Patent ↗A method of forming a 3-phenylimino-3H-phenothiazine or a 3-phenylimino-3H-phenoxazine mediator includes providing a first reactant including phenothiazine or phenoxazine, providing a first solvent, providing a second reactant and providing a second solvent. The first reactant, first solvent, second reactant and second solvent are combined to form a reactants solution. Sodium persulfate is added to the reactants solution to couple the first and second reactants resulting in a reaction solution including the 3-phenylimino-3H-phenothiazine or the 3-phenylimino-3H-phenoxazine mediator.
1. A method of forming a 3-phenylimino-3H-phenothiazine mediator, the method comprising the acts of:
providing a first reactant including phenothiazine;
providing a first solvent in which the phenothiazine has a desired solubility therein;
providing a second reactant to assist in forming the 3-phenylimino-3H-phenothiazine mediator;
providing a second solvent in which the second reactant has a desired solubility therein;
combining the first reactant, first solvent, second reactant and second solvent to form a reactants solution;
adding sodium persulfate to the reactants solution to couple the first and second reactants resulting in a reaction solution including the 3-phenylimino-3H-phenothiazine mediator; and
after adding the sodium persulfate, further processing to the reaction solution including the 3-phenylimino-3H-phenothiazine mediator so as to isolate the 3-phenylimino-3H-phenothiazine mediator.
2. The method of claim 1 , wherein the first solvent includes tetrahydrofuran (THF).
3. The method of claim 1 , wherein the second solvent includes water.
4. The method of claim 3 , wherein the second solvent further includes sodium hydroxide.
5. The method of claim 1 wherein combining the first reactant, first solvent, second reactant and second solvent including the acts of combining the first reactant and the first solvent to form a first reactant solution, and combining the second reactant and the second solvent to form a second reactant solution before the first reactant, first solvent, second reactant and second solvent are combined together to form the reactants solution.
6. The method of claim 1 , wherein further processing includes generally removing the second solvent by adding acetronitrile.
7. The method of claim 1 , wherein further processing includes generally removing the first solvent by adding ethyl acetate.
8. The method of claim 1 , wherein the second reactant includes aniline 2,5-disulfonic acid.
9. The method of claim 1 , wherein the further processing includes substantially removing at least the first solvent and second solvent from the second solution so as to isolate the 3-phenylimino-3H-phenothiazine mediator.
10. The method of claim 1 , wherein the 3-phenylimino-3H-phenothiazine mediator is in the form of a salt.
11. A method of forming and stabilizing a 3-phenylimino-3H-phenothiazine mediator, the method comprising the acts of:
providing a first reactant including phenothiazine;
providing a first solvent in which the phenothiazine has a desired solubility therein;
providing a second reactant to assist in forming the 3-phenylimino-3H-phenothiazine mediator;
providing a second solvent in which the second reactant has a desired solubility therein;
combining the first reactant, first solvent, second reactant and second solvent to form a reactants solution;
adding a coupling agent to the reactants solution to couple the first and second reactants resulting in a reaction solution including the 3-phenylimino-3H-phenothiazine mediator; and
after adding the coupling agent, further processing to the reaction solution including the 3-phenylimino-3H-phenothiazine mediator so as to isolate the 3-phenylimino-3H-phenothiazine mediator; and
stabilizing the 3-phenylimino-3H-phenothiazine mediator to a pH of from about 5 to about 8.
12. The method of claim 11 , wherein the pH is from about 5.5 to about 7.
13. The method of claim 12 , wherein the pH is from about 6 to about 7.
14. The method of claim 12 , wherein the stabilizing the 3-phenylimino-3H-phenothiazine mediator includes adding sodium hydroxide, sodium bicarbonate, sodium phosphate, tetrabutylammonium hydroxide, calcium hydroxide, potassium hydroxide, potassium phosphate, potassium bicarbonate or combinations thereof.
15. The method of claim 11 , wherein the first solvent includes tetrahydrofuran (THF).
16. The method of claim 11 , wherein the second solvent includes water.
17. The method of claim 16 , wherein the second solvent further includes sodium hydroxide.
18. The method of claim 11 , wherein the second reactant includes aniline 2,5-disulfonic acid.