US 12,351,549 B2
Agent for initiating a radical addition reaction and process using it
Virginie Belliere-Baca, Millery (FR); Olivier Peruch, Lyons (FR); Didier Morvan, Mornant (FR); and Antoine Petrelli, Lyons (FR)
Assigned to ADISSEO FRANCE S.A.S., Antony (FR)
Appl. No. 17/423,273
Filed by ADISSEO FRANCE S.A.S., Antony (FR)
PCT Filed Jan. 16, 2020, PCT No. PCT/FR2020/050059
§ 371(c)(1), (2) Date Jul. 15, 2021,
PCT Pub. No. WO2020/148509, PCT Pub. Date Jul. 23, 2020.
Claims priority of application No. 19/00461 (FR), filed on Jan. 18, 2019.
Prior Publication US 2022/0127223 A1, Apr. 28, 2022
Int. Cl. C07C 323/52 (2006.01); C07C 319/18 (2006.01); C07C 323/12 (2006.01)
CPC C07C 323/52 (2013.01) [C07C 319/18 (2013.01); C07C 323/12 (2013.01)] 6 Claims
 
1. A method for preparing a compound of formula (I)

OG Complex Work Unit Chemistry
in which
X is selected from S and Se;
R1 is selected from H and alkyl groups;
R2 is selected from H; OH; NR4R5; NHCOR4 and OCOR4; where R4 and R5 are identical or different and are selected from H and alkyl groups;
R3 is selected from OH; CH2OH; COOH; COOR6; CN; CONR4R5; and COZ, wherein R6 is selected from alkyl, R4 and R5 are as defined above, and Z represents a halide;
the method comprising the reaction of a compound of formula (II)

OG Complex Work Unit Chemistry
in which
X is selected from S and Se;
R1′ is selected from:
alkyl, groups;
thiol and thioalkyl groups when X is S; and
selenol and selenoalkyl groups when X is Se, and
R2′ is selected from H and alkyl groups;
with a compound of formula (III)

OG Complex Work Unit Chemistry
where R2 and R3 are as defined above for the compound of formula (I),
in the presence of at least one initiation agent for initiating a radical addition reaction comprising a persulfate and one or several transition metals, in elemental form or in oxidized form, said transition metal(s) being selected from Cu, Zn, Fe and their alloys in their elemental form or in an oxidized form selected from sulfates, phosphates, chlorides, carbonates, nitrites, nitrates, acetates, alcoholates, hydrogenphosphates, and hydrogen sulfates,
wherein the molar ratio of persulfate to the transition metal(s) ranges from 1:1 to 1000:1, and
wherein the reaction is carried out at a temperature from −20° C. to 40° C.