JPH01207282A - ３，４−ジ置換−ベンゾチアゾール−２−オン誘導体の新しい製造方法 - Google Patents

３，４−ジ置換−ベンゾチアゾール−２−オン誘導体の新しい製造方法

Info

Publication number: JPH01207282A
Authority: JP; Japan
Prior art keywords: acid; derivative; general formula; disubstituted; formula
Prior art date: 1987-05-01
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

JP63107371A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0416472B2 (de

Inventor

Heon-Seung Oh

呉　憲承

Kun-Ho Cho

趙　君鎬

Ki-Jong Han

韓　基鍾

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

LG Corp

Original Assignee

Lucky Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-05-01

Filing date

1988-04-28

Publication date

1989-08-21

1988-04-28 Application filed by Lucky Ltd filed Critical Lucky Ltd

1989-08-21 Publication of JPH01207282A publication Critical patent/JPH01207282A/ja

1992-03-24 Publication of JPH0416472B2 publication Critical patent/JPH0416472B2/ja

Status Granted legal-status Critical Current

Links

-1 3, 4-disubstituted- benzothiazole-2-on Chemical class 0.000 title claims abstract description 8
238000004519 manufacturing process Methods 0.000 title claims description 8
150000001875 compounds Chemical class 0.000 claims abstract description 18
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 9
229940100198 alkylating agent Drugs 0.000 claims abstract description 9
239000002168 alkylating agent Substances 0.000 claims abstract description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 6
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims abstract description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims abstract description 5
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 5
239000003377 acid catalyst Substances 0.000 claims abstract description 5
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims abstract description 5
235000019253 formic acid Nutrition 0.000 claims abstract description 5
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims abstract description 3
229960003750 ethyl chloride Drugs 0.000 claims abstract description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
229910017604 nitric acid Inorganic materials 0.000 claims abstract description 3
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 claims abstract 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims abstract 2
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 28
YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical class C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 claims description 9
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 4
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 3
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims description 3
229940008406 diethyl sulfate Drugs 0.000 claims description 3
WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 2
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
239000000126 substance Substances 0.000 claims 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
235000011054 acetic acid Nutrition 0.000 claims 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
235000006408 oxalic acid Nutrition 0.000 claims 1
DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 abstract description 3
240000007594 Oryza sativa Species 0.000 abstract description 2
235000007164 Oryza sativa Nutrition 0.000 abstract description 2
235000009566 rice Nutrition 0.000 abstract description 2
238000000034 method Methods 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
238000003756 stirring Methods 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
OEQQFQXMCPMEIH-UHFFFAOYSA-N 4-chloro-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2SC(N)=NC2=C1Cl OEQQFQXMCPMEIH-UHFFFAOYSA-N 0.000 description 2
241000251468 Actinopterygii Species 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical class C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
FVMCARDEQKVVIS-UHFFFAOYSA-N 4-bromo-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2SC(N)=NC2=C1Br FVMCARDEQKVVIS-UHFFFAOYSA-N 0.000 description 1
LDELBJIBUBHFQV-UHFFFAOYSA-N 4-chloro-3-ethyl-1,3-benzothiazol-2-one Chemical compound C1=CC=C2SC(=O)N(CC)C2=C1Cl LDELBJIBUBHFQV-UHFFFAOYSA-N 0.000 description 1
MRUMVWGVDQXKET-UHFFFAOYSA-N 4-fluoro-3-methyl-1,3-benzothiazol-2-one Chemical compound C1=CC=C2SC(=O)N(C)C2=C1F MRUMVWGVDQXKET-UHFFFAOYSA-N 0.000 description 1
GRIATXVEXOFBGO-UHFFFAOYSA-N 4-methyl-1,3-benzothiazol-2-amine Chemical compound CC1=CC=CC2=C1N=C(N)S2 GRIATXVEXOFBGO-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241000252233 Cyprinus carpio Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
238000007171 acid catalysis Methods 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
238000005815 base catalysis Methods 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229940126208 compound 22 Drugs 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000022244 formylation Effects 0.000 description 1
238000006170 formylation reaction Methods 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
230000007721 medicinal effect Effects 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000956 nontoxicity Toxicity 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
MNOALXGAYUJNKX-UHFFFAOYSA-N s-chloro chloromethanethioate Chemical compound ClSC(Cl)=O MNOALXGAYUJNKX-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical group 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
241000894007 species Species 0.000 description 1
FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical class ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Thiazole And Isothizaole Compounds (AREA)

JP63107371A 1987-05-01 1988-04-28 ３，４−ジ置換−ベンゾチアゾール−２−オン誘導体の新しい製造方法 Granted JPH01207282A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
KR1019870004299A KR900000553B1 (ko)	1987-05-01	1987-05-01	3,4-디치환-벤조티아졸-2-온 유도체의 새로운 제조방법
KR1987-4299		1987-05-01

Publications (2)

Publication Number	Publication Date
JPH01207282A true JPH01207282A (ja)	1989-08-21
JPH0416472B2 JPH0416472B2 (de)	1992-03-24

Family

ID=19261138

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP63107371A Granted JPH01207282A (ja)	1987-05-01	1988-04-28	３，４−ジ置換−ベンゾチアゾール−２−オン誘導体の新しい製造方法

Country Status (2)

Country	Link
JP (1)	JPH01207282A (de)
KR (1)	KR900000553B1 (de)

1987
- 1987-05-01 KR KR1019870004299A patent/KR900000553B1/ko not_active Expired
1988
- 1988-04-28 JP JP63107371A patent/JPH01207282A/ja active Granted

Also Published As

Publication number	Publication date
KR900000553B1 (ko)	1990-01-31
JPH0416472B2 (de)	1992-03-24
KR880013911A (ko)	1988-12-22

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JPS5922711B2 (ja)	1984-05-28	ベンゾオキサゾリノン誘導体の製造法
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JP2002114765A (ja)	2002-04-16	３−アミノ−４−カルボニルピラゾール化合物の製造方法
JPH0383969A (ja)	1991-04-09	インドール―３―カルボニトリル化合物の製造方法