Method for producing 2-hydrazinobenzothiazole derivative

Patent metadata

Field	Value
Publication number	US-10968189-B2
Application number	US-201716082471-A
Country	US
Kind code	B2
Filing date	Mar 16, 2017
Priority date	Mar 30, 2016
Publication date	Apr 6, 2021
Grant date	Apr 6, 2021

Abstract

The present invention provides a novel method for producing a 2-hydrazinobenzothiazole derivative. The present invention also provides a method for producing a compound by using the 2-hydrazinobenzothiazole derivative obtained by the production method, and a composition that contains the compound. The present invention also provides a polymerizable composition that is useful in producing film-shaped polymers and contains the compound obtained by the production method. The invention of the present application provides a method for producing a compound represented by general formula (I-C), the method including a step of reacting a compound represented by general formula (I-B) with a compound represented by general formula (I-A) in the presence of at least one compound selected from the group consisting of metal amides, metal hydrides, metal alkoxides, and organic alkali metals. A compound derived from the compound produced by the production method, and a composition that contains the compound are also provided.

First claim

The invention claimed is:

1. A method for producing a compound represented by general formula (I) below, the method comprising:
a first step of obtaining a compound represented by general formula (I-C) by reacting a compound represented by general formula (I-B) below with a compound represented by general formula (I-A) below in the presence of at least one compound selected from the group consisting of lithium amide, sodium amide, magnesium amide, potassium amide, calcium amide, cesium amide, lithium diisopropylamide, lithium hydride, sodium hydride, magnesium hydride, potassium hydride, calcium hydride, cesium hydride, lithium aluminum hydride, lithium borohydride, lithium methoxide, sodium methoxide, magnesium methoxide, potassium methoxide, calcium methoxide, cesium methoxide, lithium ethoxide, sodium ethoxide, magnesium ethoxide, potassium ethoxide, calcium ethoxide, cesium ethoxide, lithium propoxide, sodium propoxide, magnesium propoxide, potassium propoxide, calcium propoxide, cesium propoxide, lithium isopropoxide, sodium isopropoxide, magnesium isopropoxide, potassium isopropoxide, calcium isopropoxide, cesium isopropoxide, lithium butoxide, sodium butoxide, magnesium butoxide, potassium butoxide, calcium butoxide, cesium butoxide, lithium tert-butoxide, sodium tert-butoxide, magnesium tert-butoxide, potassium tert-butoxide, calcium tert-butoxide, cesium tert-butoxide, methyl lithium, ethyl lithium, propyl lithium, butyl lithium, sec-butyl lithium, tert-butyl lithium, pentyl lithium, hexyl lithium, and phenyl lithium; and
a second step of obtaining a compound represented by general formula (I) by reacting the compound represented by general formula (I-C) obtained in the first step with a compound represented by general formula (I-D) below:

where r represents an integer of 0 to 4, L W1 represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, a dimethylamino group, a diethylamino group, a diisopropylamino group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more non-adjacent —CH 2 — may each independently be substituted with —O—, —S—, —CH═CH—, —CF═CF—, or —C≡C—, any hydrogen atom in the alkyl group may be substituted with a fluorine atom, and when there are more than one L W1 , they may be the same or different,
W 2 -LG 2    (I-A)

where W 2 represents a linear or branched alkyl group having 1 to 20 carbon atoms, in which one —CH 2 — or two or more non-adjacent —CH 2 — may each independently be substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and any hydrogen atom in the alkyl group may be substituted with a fluorine atom, or W 2 may represent a group represented by P W —(Sp W —X W ) kW —, where: P W Represents a Polymerizable Group; Sp W represents a spacer group; when there are more than one Sp W , they may be the same or different; X W represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond; when there are more than one X W , they may be the same or different, however, P W —(Sp W —X W ) kW — does not contain an —O—O— bond; and kW represents an integer of 0 to 10, and

LG 2 represents a leaving group,

where, W 2 , r, and L W1 are the same as those described above,

where R 1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which any hydrogen atom may be substituted with a fluorine atom, and one —CH 2 — or two or more non-adjacent —CH 2 — may each independently be substituted with —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, or —C≡C—; or R 1 represents a group represented by P 1 —(Sp 1 -X 1 ) k1 — where: P 1 represents a polymerizable group; Sp 1 represents a spacer group; when there are more than one Sp 1 , they may be the same or different; X 1 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond; when there are more than one X 1 , they may be the same or different; and k1 represents an integer of 0 to 10,
R 2 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, in which any hydrogen atom may be substituted with a fluorine atom and one —CH 2 — or two or more non-adjacent —CH 2 — may each independently be substituted with —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, or —C≡C—; or R 2 represents a group represented by —(X 2 —Sp 2 ) k2 —P 2 where: P 2 represents a polymerizable group; Sp 2 represents a spacer group; when there are more than one Sp 2 , they may be the same or different; X 2 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond; when there are more than one X 2 , they may be the same or different; and k2 represents an integer of 0 to 10,
A 1 and A 2 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, which may be unsubstituted or substituted with one or more substituents L; when there are more than one A 1 , they may be the same or different; when there are more than one A 2 , they may be the same or different; and L represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a di

Assignees

• Dainippon Ink & Chemicals

Inventors

• Horiguchi Masahiro
• Mamiya Junichi

Classifications

• C08F2/50

  with sensitising agents · CPC title

• C09K2019/0448

  the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate · CPC title

• C09K19/38

  Polymers · CPC title

• G02F1/13363

  Birefringent elements, e.g. for optical compensation · CPC title

• C07D277/82 Primary

  Nitrogen atoms · CPC title