Process for the synthesis of lactams

Patent metadata

Field	Value
Publication number	US-11401240-B2
Application number	US-201917291043-A
Country	US
Kind code	B2
Filing date	Oct 23, 2019
Priority date	Nov 8, 2018
Publication date	Aug 2, 2022
Grant date	Aug 2, 2022

Abstract

A process for the synthesis of lactams suitable for use in antimicrobial, anti-biofilm and bacteriostatic compositions.

First claim

The invention claimed is:

1. A process for the synthesis of a lactam, the process comprising:
reacting an acetone initiator with a glyoxalic acid to produce an aldol condensate;
treating the aldol condensate with thionyl chloride; and
reacting the aldol condensate treated with thionyl chloride with ammonia or a salt thereof, to produce the lactam, wherein the reacting involves adding the ammonia or the salt thereof to the aldol condensate treated with thionyl chloride; wherein the acetone initiator is a compound with the formula:

R 2 is 4-chlorophenyl, R 4 and R 5 are H, and
the lactam produced by the process is 4-(4-chlorophenyl)-5-methylene-pyrol-2-one represented by the formula:

2. The process of claim 1 , wherein the ammonia is concentrated aqueous ammonia.

3. The process of claim 1 , wherein the process further comprises:
dehydrating the lactam to produce a lactam having an exo-methylene group.

4. The process of claim 3 , wherein the dehydrating is done with formic acid.

5. The process of claim 1 , wherein the process further comprises, prior to reacting the acetone initiator with the glyoxalic acid:
reacting an aldehyde with nitroethane; and
treating the reacted aldehyde and nitroethane with a Lewis acid to produce the acetone initiator.

Assignees

• Conopco Inc

Inventors

• Dawkins David Anthony
• Kotsakis Panagiotis
• Parry Neil James
• Thornthwaite David William

Classifications

• C07D207/27 Primary

  with substituted hydrocarbon radicals directly attached to the ring nitrogen atom · CPC title

• C07D207/44

  having three double bonds between ring members or between ring members and non-ring members · CPC title

• C07D207/38 Primary

  2-Pyrrolones · CPC title