ChemicalBook CAS DataBase List Saflufenacil

Saflufenacil synthesis

4synthesis methods

Product Name:Saflufenacil
CAS Number:372137-35-4
Molecular formula:C17H17ClF4N4O5S
Molecular Weight:500.85

854122-75-1 Synthesis

854122-75-1
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372137-35-4
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Yield:372137-35-4 84%

Reaction Conditions:

with tetrabutylammomium bromide;sodium hydroxide in tetrahydrofuran;water;toluene; pH=5.3 - 5.5 at 25 - 40;

Steps:

12
50.0 g (0.098 mol) of 2-chloro-5-[3,6-dihydro-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-N-{[methyl(1-methylethyl)amino]sulfonyl}benzamide, 3.2 g (0.0089 mol) of tetrabutylammonium bromide (=TBAB) and 15.1 g (0.12 mol) of dimethyl sulfate were introduced into the reaction vessel at 25° C. in a mixture of toluene, water and THF, and the mixture was heated to 40° C. Thereafter, a pH of 5.3-5.5 was established in the reaction mixture by addition of aqueous 10% strength NaOH solution. During the entire duration of the reaction, more aqueous 10% strength NaOH solution was added so that the pH during the entire course of the reaction was constantly at the pH which had been established beforehand. After the reaction had ended, stirring of the reaction mixture was continued for 3.5 h at 40° C. The phases were subsequently separated.55 to 60% of the solvent employed were removed from the resulting solution by distillation under atmospheric pressure, giving a hot solution of the title compound in toluene. The solution was subsequently cooled to 70° C. and then, within 5 h, and at a constant cooling rate, to 20° C., and stirring was continued for 3 h at 20° C. The solid which had precipitated was filtered off with suction and dried. This gave 42.6 g (84.0%) of the title compound as form II with an active ingredient content of 96.8%.

References:

Schmidt, Thomas;Gebhardt, Joachim;Löhr, Sandra;Keil, Michael;Wevers, Jan Hendrik;Erk, Peter;Emilia, Heidi;Hamprecht, Gerhard;Seitz, Werner;Mayer, Guido;Wolf, Bernd;Cox, Gerhard;Michel, Alfred;Zagar, Cyrill;Reinhard, Robert;Sievernich, Bernd US2010/105562, 2010, A1 Location in patent:Page/Page column 7

FullText

372136-76-0 Synthesis