Fungicidal 2-Imidazolin-5-ones and Imidazoline-5-thiones

Patent Fungicidal 2-Imidazolin-5-ones and Imidazoline-5-thiones 

Lacroix etal, US Patent 6,344,564 (February 5, 2002) Assignee Rhone-Poulenc, Inc. 

Dicyclohexylcarbodiimide (16.4 mmol) was added to a solution of the product from Step 1 (16.4 mmol) dissolved in 40 ml CH2CI2 and the mixture stirred 30 minutes at ambient temperature. Thereafter, 3-chlorophenylhydrazine (16.4 mmol) was added and the mixture heated to 30 °C 30 minutes. Insoluble material that formed was filtered off, the filtrate washed twice with 30 ml water, purified by chromatography on a silica gel, and the product isolated as a solid, mp = 146°C. 

The product from Step 2 (5 mmol) was dissolved in 30 ml xylene and refluxed 4 hours. The mixture was concentrated and triturated with 10 ml of diethyl ether whereupon the product crystallized. The precipitate was filtered and the product isolated in 56% yield, mp= 196°C. 

In an earlier investigation by the author (1) 4,4-spiro derivatives of the Step 3 product (I) were prepared. 

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