91467-19-5

Upstream product

• 79-37-8 oxalyl dichloride 
• 1932-38-3 1-phenyl-3-propylurea 
• 13140-47-1 N-n-propyl-N'-phenylthiourea 
• 91466-98-7 C₆H₇Cl₂NO₃ 
• 91467-07-1 5,5-Dichloro-3-propyl-oxazolidine-2,4-dione 
• 62-53-3 aniline 

Relevant academic research and scientific papers

Solution-phase parallel syntheses of herbicidal 1-phenyl-2,4,5- imidazolidinetriones and 2-thioxo-4,5-imidazolidinediones

In order to find new herbicidally active compounds, a fifteen-member library, focusing on the variation of 3- position substituents of 2,4,5-imidazolidine-trione or 2-thioxo-4,5-imidazolidinedione, was designed and prepared in parallel by the reaction of various ureas or thioureas with oxalyl chloride using solution-phase technology. An interesting and, to the best of our knowledge, unprecedented finding is that a by-product of 1-phenyl-3- propylcarbodiimide was formed during the addition of oxalyl chloride into the solution of 1-phenyl-3-propylthiourea in the presence of triethylamine in dichloromethane. It has been shown that the herbicidal activity of 2,4,5-imidazolidinetriones is about the same as that of their analogous 2-thioxo-4,5-imidazolidinediones. Compound with propyl or isopropyl group at the 3- position of 2,4,5-imidazolidinetrione ring demonstrated good herbicidal activity. The most active compound, 1-(2-fluoro- 4-chloro-5-propargyloxy)- phenyl-3-propyl-2-thioxo-4,5-imidazolidinedione, gave 95% control of the growth of velvetleaf at 200 g/ha in the post-emergence test.

Reaction of Oxalyl Chloride and Alkyloxalyl Chlorides with Isocyanates and Isothiocyanates

Alkyl and aryl isothiocyanates react with oxalyl chloride (1) on both double bonds of the heterocumulene to yield 3-alkyl- or 3-aryl-2,2-dichlorothiazolidine-4,5-diones 2.The two chlorines in these novel orthocarbonic acid derivatives are readily exchanged by alkoxy groups to yield 2,2-dialkoxythiazolidine-4,5-diones 3; hydrolysis of 2a (R=CH3) gave 3-methylthiazolidine-2,4,5-trione. 3-Substituted 5,5-dichlorooxazolidine-2,4-diones 8 and 5-chloro-5-alkoxyoxazolidine-2,4-diones 13 are obtained on reacting alkyl, aryl, and benzyl isocyanates with 1 and alkyloxalyl chloride, respectively.Structure assignment to these novel cycloadducts is based on IR, 1H NMR, and 13C NMR spectroscopic as well as X-ray crystallographic analysis.Formation of 8 and 13 is a stepwise process involving labile acyclic intermediates 7 and 12.The cyclizations to 8 and 13 take place only on the C=N bond of the isocyanate group.