Processes for the production of N-substituted sulfoximine pyridine N-oxides
View Patent ↗In one form, processes for the production of certain N-substituted sulfoximine N-oxides are provided. Further embodiments, forms, objects, features, advantages, aspects, and benefits shall become apparent from the description.
1. A process for preparing an N-oxidized sulfoximine compound of formula (I)
wherein
X represents NO 2 , CN, COOR 4 or CONH 2 ;
R 1 represents (C 1 -C 4 ) alkyl;
R 2 and R 3 individually represent hydrogen, methyl, ethyl, flouro, chloro or bromo;
n is an integer from 0-3;
Y represents (C 1 -C 4 ) haloalkyl, F, Cl, Br, or I; and
R 4 represents (C 1 -C 3 ) alkyl;
which includes performing an oxidation of a compound of formula (II)
wherein X, R 1 , R 2 , R 3 , n, Y and R 4 are as previously defined and the oxidation includes treating the compound of formula (II) with urea hydrogen peroxide and trifluoroacetic anhydride.
2. The process of claim 1 , wherein X represents NO 2 , CN or CONH 2 .
3. The process of claim 1 , wherein Y represents CF 3 or Cl.
4. The process of claim 1 , wherein R 2 and R 3 independently represent hydrogen, methyl or ethyl.
5. The process of claim 1 , wherein X, R 2 , R 3 , n, Y and R 4 are as previously defined, R 1 represents CH 3 , n=1-3, the compound of formula (I) has the structure
and the compound of formula (II) has the structure
6. The process of claim 5 , wherein X represents NO 2 , CN or CONH 2 , Y represents (C 1 -C 4 ) haloalkyl, and R 2 and R 3 individually represent hydrogen, methyl, ethyl, flouro, chloro or bromo.
7. The process of claim 6 , wherein X represents NO 2 , CN or CONH 2 , Y represents CF 3 , and R 2 and R 3 individually represent hydrogen, methyl or ethyl.
8. A process for preparing an N-oxidized sulfoximine compound of formula (I)
wherein
X represents NO 2 , CN, COOR 1 or CONH 2 ;
Y represents (C 1 -C 4 ) haloalkyl, F, Cl, Br, or I; and
R 1 represents (C 1 -C 4 ) alkyl;
which includes performing an oxidation of a compound of formula (II)
wherein X, Y and R 1 are as previously defined and the oxidation includes treating the compound of formula (II) with urea hydrogen peroxide and trifluoroacetic anhydride.
9. The process of claim 1 , which further includes conducting the oxidation in a polar solvent.
10. The process of claim 9 , wherein the polar solvent is selected from the group consisting of dichloromethane, tetrahydrofuran, ethyl acetate, acetone, dimethylformamide, acetonitrile, and dimethyl sulfoxide.