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US 10,851,052 B2Granted
Method for producing mercaptophenol compound and intermediate of said compound
AssigneeKumiai Chemical Industry Co., Ltd.
InventorKazuhiro Sambai
Life of this patent
Estimating the term…
Abstract
A production method in which a mercaptophenol compound is obtained using an industrially preferred sulfur atom introduction reaction, and intermediate compounds of the mercaptophenol compound are provided. A method for producing a mercaptophenol compound in which a phenyl carbamate compound is produced using a phenol compound as a raw material, and then a sulfur atom is regioselectively introduced by a reaction with sulfur monochloride, and a phenyl mercaptocarbamate compound is produced as an intermediate.
Claims16
A 5-mercaptophenyl carbamate compound represented by formula (1):
- wherein R1 and R2 each independently represent a C1-C4 alkyl group or a halogen atom,
- R3 and R4 each independently represent a hydrogen atom, a C1-C6 alkyl group that may be substituted with one or two or more identical or different halogen atoms, a C2-C6 alkenyl group that may be substituted with one or two or more identical or different halogen atoms, a C3-C6 cycloalkyl group that may be substituted with one or two or more identical or different halogen atoms, a C1-C6 alkoxy group that may be substituted with one or two or more identical or different halogen atoms, a C6-C10 aryl group that may be substituted with one or two or more identical or different substituents A, or a C6-C10 aryl C1-C4 alkyl group that may be substituted with one or two or more identical or different substituents A,
- or R3 and R4 may together form a 4- to 8-membered ring by forming a divalent group selected from the group consisting of a C3-C7 alkylene group that may be substituted with one or two or more identical or different substituents B, a —(C1-C3 alkylene)-O—(C1-C3 alkylene)- group that may be substituted with one or two or more identical or different substituents B, and a —(C1-C3 alkylene)-NH—(C1-C3 alkylene)- group that may be substituted with one or two or more identical or different substituents B,
- the substituent A represents a C1-C4 alkyl group or a halogen atom, and
- the substituent B represents a C1-C4 alkyl group, a halogen atom, or an oxo group.
2 more elements
A poly sulfide compound represented by formula (2):
- wherein R1 and R2 each independently represent a C1-C4 alkyl group or a halogen atom,
- R3 and R4 each independently represent a hydrogen atom, a C1-C6 alkyl group that may be substituted with one or two or more identical or different halogen atoms, a C2-C6 alkenyl group that may be substituted with one or two or more identical or different halogen atoms, a C3-C6 cycloalkyl group that may be substituted with one or two or more identical or different halogen atoms, a C1-C6 alkoxy group that may be substituted with one or two or more identical or different halogen atoms, a C6-C10 aryl group that may be substituted with one or two or more identical or different substituents A, or a C6-C10 aryl C1-C4 alkyl group that may be substituted with one or two or more identical or different substituents A,
- or R3 and R4 may together form a 4- to 8-membered ring by forming a divalent group selected from the group consisting of a C3-C7 alkylene group that may be substituted with one or two or more identical or different substituents B, a —(C1-C3 alkylene)-O—(C1-C3 alkylene)- group that may be substituted with one or two or more identical or different substituents B, and a —(C1-C3 alkylene)-NH—(C1-C3 alkylene)- group that may be substituted with one or two or more identical or different substituents B,
- the substituent A represents a C1-C4 alkyl group or a halogen atom,
- the substituent B represents a C1-C4 alkyl group, a halogen atom, or an oxo group, and
- n represents an integer of 2 or more,
- or a mixture thereof.
4 more elements
A method for producing a polysulfide compound represented by formula (2):
- wherein R1 and R2 each independently represent a C1-C4 alkyl group or a halogen atom,
- R3 and R4 each independently represent a hydrogen atom, a C1-C6 alkyl group that may be substituted with one or two or more identical or different halogen atoms, a C2-C6 alkenyl group that may be substituted with one or two or more identical or different halogen atoms, a C3-C6 cycloalkyl group that may be substituted with one or two or more identical or different halogen atoms, a C1-C6 alkoxy group that may be substituted with one or two or more identical or different halogen atoms, a C6-C10 aryl group that may be substituted with one or two or more identical or different substituents A, or a C6-C10 aryl C1-C4 alkyl group that may be substituted with one or two or more identical or different substituents A,
- or R3 and R4 may together form a 4- to 8-membered ring by forming a divalent group selected from the group consisting of a C3-C7 alkylene group that may be substituted with one or two or more identical or different substituents B, a —(C1-C3 alkylene)-O—(C1-C3 alkylene)- group that may be substituted with one or two or more identical or different substituents B, and a —(C1-C3 alkylene)-NH—(C1-C3 alkylene)- group that may be substituted with one or two or more identical or different substituents B,
- the substituent A represents a C1-C4 alkyl group or a halogen atom,
- the substituent B represents a C1-C4 alkyl group, a halogen atom, or an oxo group, and
- n represents an integer of 2 or more,
- or a mixture thereof, comprising the following steps:
- (i) a step of reacting a compound represented by formula (5):
- wherein R1 and R2 are as defined above,
- with a carbamoyl halide compound represented by formula (a):
- wherein R3 and R4 are as defined above, and X represents a halogen atom,
- in the presence of a base to produce a compound represented by formula (3):
- wherein R1, R2, R3, and R4 are as defined above;
- and
- (ii) a step of subjecting the compound represented by the formula (3) to a reaction with a sulfur compound in the presence of an acid to produce the compound represented by the formula (2).
12 more elements
A method for producing a 5-mercaptophenyl carbamate compound represented by formula (1):
- wherein R1 and R2 each independently represent a C1-C4 alkyl group or a halogen atom,
- R3 and R4 each independently represent a hydrogen atom, a C1-C6 alkyl group that may be substituted with one or two or more identical or different halogen atoms, a C2-C6 alkenyl group that may be substituted with one or two or more identical or different halogen atoms, a C3-C6 cycloalkyl group that may be substituted with one or two or more identical or different halogen atoms, a C1-C6 alkoxy group that may be substituted with one or two or more identical or different halogen atoms, a C6-C10 aryl group that may be substituted with one or two or more identical or different substituents A, or a C6-C10 aryl C1-C4 alkyl group that may be substituted with one or two or more identical or different substituents A,
- or R3 and R4 may together form a 4- to 8-membered ring by forming a divalent group selected from the group consisting of a C3-C7 alkylene group that may be substituted with one or two or more identical or different substituents B, a —(C1-C3 alkylene)-O—(C1-C3 alkylene)- group that may be substituted with one or two or more identical or different substituents B, and a —(C1-C3 alkylene)-NH—(C1-C3 alkylene)- group that may be substituted with one or two or more identical or different substituents B,
- the substituent A represents a C1-C4 alkyl group or a halogen atom, and
- the substituent B represents a C1-C4 alkyl group, a halogen atom, or an oxo group, comprising the following steps:
- (i) a step of reacting a compound represented by formula (5):
- wherein R1 and R2 are as defined above,
- with a carbamoyl halide compound represented by formula (a):
- wherein R3 and R4 are as defined above, and X represents a halogen atom,
- in the presence of a base to produce a compound represented by formula (3):
- wherein R1, R2, R3, and R4 are as defined above;
- (ii) a step of subjecting the compound represented by the formula (3) to a reaction with a sulfur compound in the presence of an acid to produce a polysulfide compound represented by formula (2):
- wherein R1, R2, R3, and R4 are as defined above, and n represents an integer of 2 or more, or a mixture thereof;
- and
- (iii) a step of producing the compound represented by the formula (1) from the compound represented by the formula (2).
12 more elements
A method for producing a mercaptophenol compound represented by formula (4):
- wherein R1 and R2 each independently represent a C1-C4 alkyl group or a halogen atom, comprising the following steps:
- (i) a step of reacting a compound represented by formula (5):
- wherein R1 and R2 are as defined above,
- with a carbamoyl halide compound represented by formula (a):
- wherein R3 and R4 each independently represent a hydrogen atom, a C1-C6 alkyl group that may be substituted with one or two or more identical or different halogen atoms, a C2-C6 alkenyl group that may be substituted with one or two or more identical or different halogen atoms, a C3-C6 cycloalkyl group that may be substituted with one or two or more identical or different halogen atoms, a C1-C6 alkoxy group that may be substituted with one or two or more identical or different halogen atoms, a C6-C10 aryl group that may be substituted with one or two or more identical or different substituents A, or a C6-C10 aryl C1-C4 alkyl group that may be substituted with one or two or more identical or different substituents A,
- or R3 and R4 may together form a 4- to 8-membered ring by forming a divalent group selected from the group consisting of a C3-C7 alkylene group that may be substituted with one or two or more identical or different substituents B, a —(C1-C3 alkylene)-O—(C1-C3 alkylene)- group that may be substituted with one or two or more identical or different substituents B, and a —(C1-C3 alkylene)-NH—(C1-C3 alkylene)- group that may be substituted with one or two or more identical or different substituents B,
- the substituent A represents a C1-C4 alkyl group or a halogen atom,
- the substituent B represents a C1-C4 alkyl group, a halogen atom, or an oxo group, and
- X represents a halogen atom,
- in the presence of a base to produce a compound represented by formula (3):
- wherein R1, R2, R3, and R4 are as defined above;
- (ii) a step of subjecting the compound represented by the formula (3) to a reaction with a sulfur compound in the presence of an acid to produce a compound represented by formula (2):
- wherein R1, R2, R3, and R4 are as defined above, and n represents an integer of 2 or more;
- (iii) a step of producing a compound represented by formula (1):
- wherein R1, R2, R3, and R4 are as defined above,
- from the compound represented by the formula (2);
- and
- (iv) a step of producing the compound represented by the formula (4) from the compound represented by the formula (1).
15 more elements
Dependencies are inferred from the claim text.