ChemicalBook CAS DataBase List Ethametsulfuron-methyl

Ethametsulfuron-methyl synthesis

1synthesis methods

Product Name:Ethametsulfuron-methyl
CAS Number:97780-06-8
Molecular formula:C15H18N6O6S
Molecular Weight:410.4

Ethametsulfuron-methyl via a multi-step sulfonylurea synthesis starting from 2-amino-4-methoxy-6-methyl-1,3,5-triazine, which is sulfonylated with 2-(ethoxycarbonyl)ethylsulfonyl chloride in the presence of a base to form the sulfonamide. This intermediate is activated with phosgene or triphosgene to generate the sulfonyl isocyanate, which undergoes condensation with methyl 2-amino-4-methoxy-6-methyl-1,3,5-triazine-5-carboxylate under controlled conditions to construct the urea bridge. Final hydrolysis, methyl esterification, and recrystallization yield ethametsulfuron-methyl.

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2-Amino-4-methylamino-6-ethoxy-1,3,5-triazine

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Yield:-

Reaction Conditions:

in dichloromethane

Steps:

1 Methyl 2-[[(4-ethoxy-6-methylamino-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoate
EXAMPLE 1 Methyl 2-[[(4-ethoxy-6-methylamino-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoate To a suspension of 0.8 g of 4-ethoxy-6-methylamino-1,3,5-triazin-2-amine in 25 ml of methylene chloride was added 1.14 g of 2-(methoxycarbonyl)benzenesulfonyl isocyanate. Dissolution of the suspension occurred, followed by precipitation of a solid. After 1 hour at ambient temperature, the solid was collected and dried giving 0.9 g of the title compound, m.p. 204°-206° C. IR (nujol mull) C=O (1700 and 1730 cm^-1).

References:

E. I. Du Pont de Nemours and Company US4548638, 1985, A

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Ethametsulfuron-methyl Related Search:

Methyl acetate Paraquat dichloride Methylparaben Methanol 4-Aminobenzoic acid Acetonitrile 2-Carbomethoxybenzenesulfonamide 2-Carboxy phenylsulfamide 2,4-Diamino-6-methoxy-1,3,5-triazine

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