Phosgene → 9-[4-Chloro-2-fluoro-5-(1-methoxycarbonyl-cyclopropylthio)-phenylimino]-8-thia-1,6-diazabicyclo[4.3.0]nonan-7-one

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Reaction Steps

While stirring at a temperature of from 0° to +10° C., 5.7 ml of a 20% solution of phosgene in toluene are added dropwise to a solution of 3.7 g of 1-[2-chloro-4-fluoro-5-(1-hexahydropyridazinyl-thiocarbonylamino)-phenylthio]-cyclopropanecarboxylic acid methyl ester and 4.6 ml of triethylamine in 100 ml of toluene. The reaction mixture is then stirred for 4 hours and then introduced into ice-water. The organic phase is then separated off and dried over sodium sulfate. Concentration by evaporation and subsequent chromatographic purification by means of silica gel chromatography yield 3.7 g of 9-[4-chloro-2-fluoro-5-(1-methoxycarbonyl-cyclopropylthio)-phenylimino]-8-thia-1,6-diazabicyclo[4.3.0]nonan-7-one, having a melting point of +149° C.

Provenance & Evidence