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ChemicalBook CAS DataBase List Sulfometuron-methyl
74222-97-2

Sulfometuron-methyl synthesis

4synthesis methods
Sulfometuron-methyl is produced by reaction of 2-sulfonylisocyanate methylbenzoate with 2-amino-4,6-dimethylpyrimidine.
-

Yield:74222-97-2 98%

Reaction Conditions:

in acetonitrile

Steps:

1 Preparation of 2-[[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester
EXAMPLE 1 Preparation of 2-[[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester A slurry of 7.0 grams (0.057 moles) of 4,6-dimethyl-2-pyrimidinamine, 6.0 grams (0.092 moles) sodium cyanate, and 13.5 grams (0.057 moles) 2-carbomethoxybenzenesulfonyl chloride in 60 ml acetonitrile was stirred 1 hour at reflux (81°). The reaction was diluted with 60 ml water, allowed to cool to room temperature and filtered. The solid was washed with 20 ml water and dried. There was obtained 16.0 grams (77.0% of theory) of the title compound. The product was 98% pure as assayed by high pressure liquid chromatography. The m.p. and IR spectrum of the title compound were identical to those of an authentic sample prepared as described in U.S. Pat. No. 4,394,506.

References:

E. I. Du Pont de Nemours and Company US4546179, 1985, A

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