Chalcogen-containing organic compound and a use thereof
AssigneesJnc Corporation, Pi-Crystal Incorporation
InventorsJunichi Takeya, Toshihiro Okamoto, Chikahiko Mitsui, Takeshi Matsushita
Life of this patent
Estimating the term…
Abstract
A compound is represented by Formula (1): wherein, each X is independently oxygen, sulfur, or selenium; m is 0 or 1; each n is independently 0 or 1; R1-R3 are each independently, for example, hydrogen or alkyl having 1 to 20 carbons; wherein (i) in the case of m=0, it is excluded that all of R1-R3 are hydrogen at the same time; (ii) in the case of m=0, n=0 and in the case that m is 0, one of n is 0 and the other is 1, it is excluded that “both of X are sulfur and all R3s are the same atoms or groups at the same time”; (iii) in the case of m=0, n=1, it is excluded that all R3s are the same atoms or groups at the same time, and at least one of R3s is hydrogen.
Claims9
A compound represented by Formula (1-1) or Formula (1-2):
- wherein, in Formula (1-1) and Formula (1-2), each X is independently sulfur, or selenium;
- m is 0 or 1;
- each n existing at two positions is 0;
- and each R3 existing at two positions is independently fluorine, alkyl having 1 to 20 carbons, aryl, pyridyl, furyl, thienyl or thiazolyl, wherein at least one hydrogen in the alkyl may be replaced with fluorine, and at least one hydrogen on a ring of the aryl, pyridyl, furyl, thienyl and thiazolyl may be replaced with at least one selected from the group consisting of fluorine and alkyl having 1 to 10 carbons.
A method for producing a compound represented by Formula (1):
- wherein, in Formula (1), each X is independently sulfur, or selenium;
- m is 0 or 1;
- each n existing at two positions is independently 0 or 1;
- R1-R3 are each independently hydrogen, fluorine, alkyl having 1 to 20 carbons, aryl, pyridyl, furyl, thienyl or thiazolyl, wherein at least one hydrogen in the alkyl may be replaced with fluorine, and at least one hydrogen on a ring of the aryl, pyridyl, furyl, thienyl and thiazolyl may be replaced with at least one selected from the group consisting of fluorine and alkyl having 1 to 10 carbons;
- wherein
- (i) in the case of m=0, it is excluded that all of R1-R3 are hydrogen at the same time;
- (ii) in the case that m is 0 and both of n are 0, and in the case that m is 0, one of n is 0 and the other is 1, it is excluded that both of X are sulfur and all R3s are the same atoms or groups at the same time;
- (iii) in the case that m is 0 and both of n are 1, it is excluded that all R3s are the same atoms or groups at the same time, and at least one of R3s is hydrogen,
- wherein the method comprises:
- a step of cross-coupling a compound represented by Formula (11) and a compound represented by Formula (12) to obtain a compound represented by Formula (13);
- a step of deprotecting a methoxy from the compound represented by Formula (13) to obtain a compound represented by Formula (14);
- a step of allowing the compound represented by Formula (14) to react with N,N-dialkyl carbamoylthiochloride or N,N-dialkyl carbamoylselenochloride to obtain a compound represented by Formula (15);
- and
- a step of heating the compound represented by Formula (15) to obtain the compound represented by Formula (1),
- wherein, in Formulae (11)-(15), the definitions of m, n and R1-R3 are the same as the corresponding symbols in Formula (1) respectively, Me is methyl, Hal is bromine or iodine, and each R is independently alkyl having 1-3 carbons.
A method for producing a compound represented by Formula (1):
- wherein, in Formula (1), each X is oxygen;
- m is 0 or 1;
- each n existing at two positions is independently 0 or 1;
- R1-R3 are each independently hydrogen, fluorine, alkyl having 1 to 20 carbons, aryl, pyridyl, furyl, thienyl or thiazolyl, wherein at least one hydrogen in the alkyl may be replaced with fluorine, and at least one hydrogen on a ring of the aryl, pyridyl, furyl, thienyl and thiazolyl may be replaced with at least one selected from the group consisting of fluorine and alkyl having 1 to 10 carbons;
- wherein
- (i) in the case of m=0, it is excluded that all of R1-R3 are hydrogen at the same time;
- (ii) in the case that m is 0 and both of n are 1, it is excluded that all R3s are the same atoms or groups at the same time, and at least one of R3s is hydrogen,
- wherein the method comprises:
- a step of cross-coupling a compound represented by Formula (11) and a compound represented by Formula (12) to obtain a compound represented by Formula (13);
- a step of deprotecting a methoxy from the compound represented by Formula (13) to obtain a compound represented by Formula (14);
- and
- a step of heating and dehydrating the compound represented by Formula (14) under a zeolite catalyst to obtain the compound represented by Formula (1),
- wherein, in Formulae (11)-(14), the definitions of m, n and R1-R3 are the same as the corresponding symbols in Formula (1) respectively, Me is methyl, and Hal is bromine or iodine.
Dependencies are inferred from the claim text.