The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Date of Patent:
Nov. 20, 2018

Filed:

Mar. 12, 2018
Applicant:

The United States of America As Represented BY the Secretary of the Navy, Washington, DC (US);

Inventors:

Patrick A. Caruana, LaPlata, MD (US);

Alfred G. Stern, Upper Marlboro, MD (US);

Alex J. Zaita, Houston, TX (US);

Thao Vo, Portland, OR (US);

Attorney:
Primary Examiner:
Int. Cl.
CPC ...
C07D 239/42 (2006.01);
U.S. Cl.
CPC ...
C07D 239/42 (2013.01);
Abstract

A synthesis for an azo intermediate, 5,5'-azobis(4-chloropyrimidine) is disclosed. 5,5′-azobis(4-chloropyrimidine) is a relatively stable azo compound in that decomposition does not occur until about 194° C. 5,5′-azobis(4-chloropyrimidine) is a product of oxidative dimerization of 5-amino-4-pyrimidine, which a water soluble compound. The azo intermediate is formed in an aqueous solution, but the azo intermediate is substantially insoluble in water; and as it forms it separates producing a reaction mixture that is a slurry. The azo intermediate is isolated by filtration. The azo intermediate is marginally soluble in acetone. The yield is at least 18%, and the oxidizing agent (bleach) is inexpensive, reaction conditions do not require extreme heat or cold, which taken together make the azo intermediate suitable for scaling up.


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