Process for the selective chlorination of 4,5-dihydro-1-phenyl-1

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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C07D24912

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054688680

ABSTRACT:
This invention provides a process for optimizing the yield of a 1-(2,4-dichlorophenyl)-4,5-dihydro-1H-1,2,4-triazol-5-one by the chlorination in two steps of a 4,5-dihydro-1-phenyl-1H-1,2,4-triazol-5-one. The critical first step is the selective chlorination of the phenyl ring in the 4-position by addition of chlorine to a solution of the 4,5-dihydro-1-phenyl-1H-1,2,4-triazol-5-one in N,N-dimethylformamide. Chlorination of the product of the first step in acetic acid/water yields the 1-(2,4-dichlorophenyl)-4,5-dihydro-1H-1,2,4-triazol-5-one in high yield.

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patent: 4980480 (1990-12-01), Theodoridis
J. Am. Chem. Soc., 74, 3171 (1952) Adams & Braun.
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Bull. Chem. Soc. Japan, 1970, 43(10), 3318 Seguchi et al.
J. Am. Chem. Soc., 83, 4605 (1961) Stock et al.
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