Piroctone Olamine Synthetic Routes

2023/11/01


Piroctone olamine can be synthesized through a variety of routes, but the most common method involves the reaction of 2-amino-4-nitrophenol with chloroacetamide to produce 2-(2,4-dinitroanilino)-2-imidazoline, which is then reacted with 2-aminoethanol to form piroctone olamine.

Another synthetic route involves the reaction of 2-amino-4-nitrophenol with chloroacetic acid to produce 2-(2,4-dinitroanilino)-2-hydroxyacetic acid, which is then converted to piroctone olamine through a series of steps involving phosphorus oxychloride, ammonia, and potassium hydroxide.

There are also other routes as follows:

1.One method involves the reaction of 2-amino-4-nitrophenol with chloroacetyl chloride to produce 2-(2,4-dinitroanilino)-N-(chloroacetyl)acetamide, which is then reacted with 2-aminoethanol to form piroctone olamine.

2.Another method involves the reaction of 2-amino-4-nitrophenol with chloroacetic acid to produce 2-(2,4-dinitroanilino)-2-hydroxyacetic acid, which is then reduced with sodium borohydride to form 2-(2,4-dinitroanilino)-2-hydroxyethylamine. This compound is then reacted with chloroacetyl chloride to form 2-(2,4-dinitroanilino)-N-(chloroacetyl)-2-hydroxyethylamine, which is finally reacted with ammonia to form piroctone olamine.

3.A third method involves the reaction of 2-amino-4-nitrophenol with chloroacetic acid to produce 2-(2,4-dinitroanilino)-2-hydroxyacetic acid, which is then reacted with thionyl chloride to form 2-(2,4-dinitroanilino)-2-chloroacetyl chloride. This compound is then reacted with 2-aminoethanol to form piroctone olamine.

These are just a few examples of the different synthetic routes that have been reported in the literature for the synthesis of piroctone olamine.

Piroctone olamine is a chemical compound that is used primarily in the cosmetic and personal care industries. Its main application is as an anti-dandruff agent in shampoos and other hair care products. Piroctone olamine works by inhibiting the growth of the yeast Malassezia, which is a common cause of dandruff.

In addition to its anti-dandruff properties, piroctone olamine has also been used as a preservative in cosmetic products, as well as in the treatment of seborrheic dermatitis, a skin condition that causes red, scaly patches on the scalp, face, and other areas of the body.

One of the advantages of piroctone olamine is that it is generally considered to be safe and well-tolerated by most people, with few reported side effects. It is also effective at relatively low concentrations, which can help to minimize the risk of skin irritation or other adverse reactions.

However, one potential disadvantage of piroctone olamine is that it may not be as effective as some other anti-dandruff agents, such as ketoconazole or selenium sulfide. Additionally, some people may be allergic or sensitive to piroctone olamine, and may experience skin irritation or other adverse reactions as a result.

Key words:

Piroctone olamine