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US 11,643,673 B2Granted
Functionalised cyclic dithiocarbamate synthesis method
AssigneeArkema France
InventorsGeorges Fremy, Arnaud Masselin
Life of this patent
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Abstract
Provided is a process for synthesizing a functionalized cyclic dithiocarbamate.
Claims6
A process for synthesizing a functionalized cyclic dithiocarbamate of formula (I):
- in which
- R1 is a hydrogen or an aromatic or nonaromatic, linear or cyclic, saturated or unsaturated, branched or unbranched, hydrocarbon-based chain including from 1 to 20 carbon atoms, and which may, optionally, include one or more heteroatoms chosen from O, S, N, P and Si;
- X represents —C(═O)— or —CH2— or —CN;
- R2 is (i) either nonexistent (when X represents —CN), (ii) or a hydrogen, (iii) or —OR3, R3 being a hydrogen or an aromatic or nonaromatic, linear or cyclic, saturated or unsaturated, branched or unbranched, hydrocarbon-based chain including from 1 to 20 carbon atoms, and which may, optionally, comprise or more heteroatoms chosen from O, S, N, P and Si, (iv) or —NR4R5, with R4 and R5, which are the same or different, being a hydrogen or an aromatic or nonaromatic, linear or cyclic, saturated or unsaturated, branched or unbranched, hydrocarbon-based chain including from 1 to 20 carbon atoms, and which may, optionally, include one or more heteroatoms chosen from O, S, N, P and Si;
- n is equal to 0, 1 or 2;
- and
- represents an asymmetric carbon;
- said process comprising the steps of:
- a/ providing at least one compound of formula (II):
- G-(CH2)n—C*H(NHR1)—X—R2 (II)
- in which
- n, R1, R2, X and * are as defined previously,
- G represents either (i) R6—C(═O)—O—CH2—, or (ii) (R7O)(R8O)—P(═O)—O—CH2—, or (iii) R7O—SO2—O—CH2—;
- R6 is a hydrogen or an aromatic or nonaromatic, linear or cyclic, saturated or unsaturated, branched or unbranched, hydrocarbon-based chain including from 1 to 20 carbon atoms, and which may, optionally, include one or more heteroatoms chosen from O, S, N, P and Si;
- R7 and R8, which may be identical or different, are chosen, independently of each other, from a proton H, an alkali metal, an alkaline-earth metal or an ammonium;
- b/ providing at least one inorganic trithiocarbonate;
- c/ reaction between said at least compound of formula (II) and said at least inorganic trithiocarbonate in the presence of at least one enzyme chosen from sulfhydrylases;
- d/ production of at least one functionalized cyclic dithiocarbamate of formula (I);
- e/ separation and isolation of said at least one functionalized cyclic dithiocarbamate of formula (I),
- f/ optionally, additional functionalization of the functionalized cyclic dithiocarbamate of formula (I) obtained in step d/ or e/;
- steps a/ and b/ optionally being performed simultaneously.
18 more elements
Dependencies are inferred from the claim text.