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ChemicalBook CAS DataBase List Pyrazosulfuron-ethyl
93697-74-6

Pyrazosulfuron-ethyl synthesis

2synthesis methods
Pyrazosulfuron-ethyl is commercially produced via a sulfonylurea synthesis starting from ethyl 5-amino-1-methylpyrazole-4-carboxylate, which is sulfonylated with 2-(chlorosulfonyl)benzoic acid ethyl ester under basic conditions to form the sulfonamide. This intermediate is activated with phosgene or triphosgene to generate the sulfonyl isocyanate, which undergoes condensation with 2-amino-4,6-dimethoxypyrimidine to construct the urea bridge. Final cyclisation, hydrolysis, and recrystallisation yield pyrazosulfuron-ethyl.
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Yield:-

Reaction Conditions:

in acetonitrile

Steps:

7 Synthesis of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide (Compound No. 835):
The above crude sulfonyl isocyanate (0.98 g) was added to a solution of 0.4 g of 2-amino-4,6-dimethoxy pyrimidine in 20 ml of dry acetonitrile and the mixture was stirred at room temperature. The crystals formed were filtered, washed and dried to obtain 0.8 g of the title compound melting at 170°-172° C.

References:

Nissan Chemical Industries, Ltd. US4954164, 1990, A

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