JPS59137475A - ベンゾチアゾ−ルの製法 - Google Patents

ベンゾチアゾ−ルの製法

Info

Publication number: JPS59137475A
Authority: JP; Japan
Prior art keywords: formula; compound; alkyl; group; reaction
Prior art date: 1983-01-21
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

JP492084A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0576474B2 (cs

Inventor

ライナ−・ハンプレヒト

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.)

Bayer AG

Original Assignee

Bayer AG

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.)

1983-01-21

Filing date

1984-01-17

Publication date

1984-08-07

1984-01-17 Application filed by Bayer AG filed Critical Bayer AG

1984-08-07 Publication of JPS59137475A publication Critical patent/JPS59137475A/ja

1993-10-22 Publication of JPH0576474B2 publication Critical patent/JPH0576474B2/ja

Status Granted legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 7
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title claims 4
150000001875 compounds Chemical class 0.000 claims description 29
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 28
239000000203 mixture Substances 0.000 claims description 21
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 16
238000000034 method Methods 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
-1 benzo compound Chemical class 0.000 claims description 4
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
238000003776 cleavage reaction Methods 0.000 claims description 2
230000007017 scission Effects 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
150000002736 metal compounds Chemical class 0.000 claims 1
150000002825 nitriles Chemical class 0.000 claims 1
150000003557 thiazoles Chemical class 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
239000007787 solid Substances 0.000 description 14
238000002360 preparation method Methods 0.000 description 13
FISVWAMPAATJLP-UHFFFAOYSA-N 5-nitro-1,3-benzothiazol-2-amine Chemical compound [O-][N+](=O)C1=CC=C2SC(N)=NC2=C1 FISVWAMPAATJLP-UHFFFAOYSA-N 0.000 description 12
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
238000003756 stirring Methods 0.000 description 10
239000000243 solution Substances 0.000 description 9
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 9
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
239000000047 product Substances 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
TVKDOFDAJFFGBZ-UHFFFAOYSA-N 5-(benzenesulfonyl)-1,3-benzothiazol-2-amine Chemical compound C=1C=C2SC(N)=NC2=CC=1S(=O)(=O)C1=CC=CC=C1 TVKDOFDAJFFGBZ-UHFFFAOYSA-N 0.000 description 2
PCTSJTFLYMKLEW-UHFFFAOYSA-N 5-(chloromethylsulfonyl)-1,3-benzothiazol-2-amine Chemical compound ClCS(=O)(=O)C1=CC=C2SC(N)=NC2=C1 PCTSJTFLYMKLEW-UHFFFAOYSA-N 0.000 description 2
AOJGGKMMKJRALW-UHFFFAOYSA-N 5-ethylsulfonyl-1,3-benzothiazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C2SC(N)=NC2=C1 AOJGGKMMKJRALW-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 2
150000001448 anilines Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000001035 drying Methods 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
YSEMNCKHWQEMTC-UHFFFAOYSA-N 1-chloro-4-(4-chloro-3-nitrophenyl)sulfonyl-2-nitrobenzene Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(S(=O)(=O)C=2C=C(C(Cl)=CC=2)[N+]([O-])=O)=C1 YSEMNCKHWQEMTC-UHFFFAOYSA-N 0.000 description 1
YGYZHNBAXADALT-UHFFFAOYSA-N 1-chloro-4-(chloromethylsulfonyl)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)CCl)=CC=C1Cl YGYZHNBAXADALT-UHFFFAOYSA-N 0.000 description 1
VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 1
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
RLXKADBMLQPLDV-UHFFFAOYSA-N 2-chloro-1,5-dinitro-3-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C(C(F)(F)F)=C1 RLXKADBMLQPLDV-UHFFFAOYSA-N 0.000 description 1
KWIXNFOTNVKIGM-UHFFFAOYSA-N 2-chloro-5-nitroaniline Chemical compound NC1=CC([N+]([O-])=O)=CC=C1Cl KWIXNFOTNVKIGM-UHFFFAOYSA-N 0.000 description 1
VEWGTWPJKSPGCD-UHFFFAOYSA-N 2-methyl-5-nitro-1,3-benzothiazole Chemical compound [O-][N+](=O)C1=CC=C2SC(C)=NC2=C1 VEWGTWPJKSPGCD-UHFFFAOYSA-N 0.000 description 1
NSYKYZBOQLCIHR-UHFFFAOYSA-N 2-nitro-1,3-benzothiazole Chemical compound C1=CC=C2SC([N+](=O)[O-])=NC2=C1 NSYKYZBOQLCIHR-UHFFFAOYSA-N 0.000 description 1
UUPFVBYGXASING-UHFFFAOYSA-N 5-nitro-7-(trifluoromethyl)-1,3-benzothiazol-2-amine Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C2SC(N)=NC2=C1 UUPFVBYGXASING-UHFFFAOYSA-N 0.000 description 1
BHCMLNCYXIFSPT-UHFFFAOYSA-N 7-nitro-5-(trifluoromethyl)-1,3-benzothiazol-2-amine Chemical compound FC(F)(F)C1=CC([N+]([O-])=O)=C2SC(N)=NC2=C1 BHCMLNCYXIFSPT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000000987 azo dye Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
150000003950 cyclic amides Chemical class 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
TWKKUWBBCHHMLT-UHFFFAOYSA-N disodium;sulfide;trihydrate Chemical compound O.O.O.[Na+].[Na+].[S-2] TWKKUWBBCHHMLT-UHFFFAOYSA-N 0.000 description 1
125000006575 electron-withdrawing group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000434 metal complex dye Substances 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000010421 standard material Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
150000003556 thioamides Chemical class 0.000 description 1
150000003567 thiocyanates Chemical class 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
125000004417 unsaturated alkyl group Chemical group 0.000 description 1

Landscapes

Thiazole And Isothizaole Compounds (AREA)

JP492084A 1983-01-21 1984-01-17 ベンゾチアゾ−ルの製法 Granted JPS59137475A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE3301869.3		1983-01-21
DE3301869		1983-01-21
DE3337859.2		1983-10-18

Publications (2)

Publication Number	Publication Date
JPS59137475A true JPS59137475A (ja)	1984-08-07
JPH0576474B2 JPH0576474B2 (cs)	1993-10-22

Family

ID=6188793

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP492084A Granted JPS59137475A (ja)	1983-01-21	1984-01-17	ベンゾチアゾ−ルの製法

Country Status (1)

Country	Link
JP (1)	JPS59137475A (cs)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4910672A (cs) *	1972-05-24	1974-01-30
JPS57185264A (en) *	1981-05-01	1982-11-15	Uniroyal Inc	Manufacture of pentaheterocyclic compound

1984
- 1984-01-17 JP JP492084A patent/JPS59137475A/ja active Granted

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4910672A (cs) *	1972-05-24	1974-01-30
JPS57185264A (en) *	1981-05-01	1982-11-15	Uniroyal Inc	Manufacture of pentaheterocyclic compound

Also Published As

Publication number	Publication date
JPH0576474B2 (cs)	1993-10-22

Publication	Publication Date	Title
JPH0153276B2 (cs)	1989-11-13
Fekri et al.	2020	Urazolium diacetate as a new, efficient and reusable Brønsted acid ionic liquid for the synthesis of novel derivatives of thiazolidine-4-ones
Middleton	1966	Reactions of 2, 2-Dicyano-3, 3-bis (trifluoromethyl) oxirane with Thiocarbonyl Compounds1
HU198029B (en)	1989-07-28	Process for production of 1,2-bensiztiasolones
CA1078847A (en)	1980-06-03	4-(sulfamoyl-phenyl)-4-hydroxythiazolidine derivatives
US4000135A (en)	1976-12-28	Manufacture of basic dyes by catalytic oxidation
CA2188967A1 (en)	1997-05-23	Method for the preparation of substituted 3-(phenylimino)-3h-phenothiazines and phenoxazines
US4808723A (en)	1989-02-28	Process for the preparation of benzothiazoles
JPS59137475A (ja)	1984-08-07	ベンゾチアゾ−ルの製法
NODIFF et al.	1961	Synthesis of Phenothiazines. V. 1 Some Halogen-Containing Phenothiazines2
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US5371232A (en)	1994-12-06	Preparation of 2-(4-aminophenyl)benzothiazole compounds
US4099008A (en)	1978-07-04	Process for the preparation of 3-(3,5-dichlorophenyl)-hydantoin
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US4257944A (en)	1981-03-24	Process for the manufacture of cyano azo dyes
Seligman et al.	1953	Some Derivatives of p-Aminosalicylic Acid1
Kuznetsova et al.	1969	Synthesis and properties of derivatives of 2-mercaptobenzothiazole: VIII.(Perhydro-1, 3-thiazino)[2, 3-b] benzothiazolines