DE2609864C2 - Verfahren zur Herstellung von 3-Amino-1,2-benzisothiazolen - Google Patents
Verfahren zur Herstellung von 3-Amino-1,2-benzisothiazolenInfo
- Publication number
- DE2609864C2 DE2609864C2 DE2609864A DE2609864A DE2609864C2 DE 2609864 C2 DE2609864 C2 DE 2609864C2 DE 2609864 A DE2609864 A DE 2609864A DE 2609864 A DE2609864 A DE 2609864A DE 2609864 C2 DE2609864 C2 DE 2609864C2
- Authority
- DE
- Germany
- Prior art keywords
- benzisothiazoles
- amino
- reaction
- radical
- ammonia
- Prior art date
- 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.)
- Expired
Links
- WIJQCPIRWXSWQG-UHFFFAOYSA-N 1,2-benzothiazol-3-amine Chemical class C1=CC=C2C(N)=NSC2=C1 WIJQCPIRWXSWQG-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229910021529 ammonia Inorganic materials 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229920000137 polyphosphoric acid Polymers 0.000 claims 1
- -1 aromatic radical Chemical class 0.000 description 14
- 239000007858 starting material Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- NHWQMJMIYICNBP-UHFFFAOYSA-N 2-chlorobenzonitrile Chemical compound ClC1=CC=CC=C1C#N NHWQMJMIYICNBP-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BAKAGHXBJJLTDB-UHFFFAOYSA-N 1,2-benzothiazole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=NSC2=C1 BAKAGHXBJJLTDB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- UWPBZQSTQOKGLK-UHFFFAOYSA-N 1-chloronaphthalene-2-carbonitrile Chemical compound C1=CC=C2C(Cl)=C(C#N)C=CC2=C1 UWPBZQSTQOKGLK-UHFFFAOYSA-N 0.000 description 1
- PZHIWRCQKBBTOW-UHFFFAOYSA-N 1-ethoxybutane Chemical compound CCCCOCC PZHIWRCQKBBTOW-UHFFFAOYSA-N 0.000 description 1
- NVJUHMXYKCUMQA-UHFFFAOYSA-N 1-ethoxypropane Chemical compound CCCOCC NVJUHMXYKCUMQA-UHFFFAOYSA-N 0.000 description 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- AFMPMSCZPVNPEM-UHFFFAOYSA-N 2-bromobenzonitrile Chemical compound BrC1=CC=CC=C1C#N AFMPMSCZPVNPEM-UHFFFAOYSA-N 0.000 description 1
- MJWHJRQCPXYBFJ-UHFFFAOYSA-N 2-chloro-9,10-dioxoanthracene-1-carbonitrile Chemical compound C1=CC=C2C(=O)C3=C(C#N)C(Cl)=CC=C3C(=O)C2=C1 MJWHJRQCPXYBFJ-UHFFFAOYSA-N 0.000 description 1
- OHMGMEZIJDNQAW-UHFFFAOYSA-N 2-chloroanthracene-1-carbonitrile Chemical compound C1=CC=CC2=CC3=C(C#N)C(Cl)=CC=C3C=C21 OHMGMEZIJDNQAW-UHFFFAOYSA-N 0.000 description 1
- QKFGNYSVQDDQIA-UHFFFAOYSA-N 2-chloronaphthalene-1-carbonitrile Chemical compound C1=CC=CC2=C(C#N)C(Cl)=CC=C21 QKFGNYSVQDDQIA-UHFFFAOYSA-N 0.000 description 1
- VWHFWJJFNGVEMB-UHFFFAOYSA-N 2-chlorophenanthrene-1-carbonitrile Chemical compound C1=CC=C2C3=CC=C(Cl)C(C#N)=C3C=CC2=C1 VWHFWJJFNGVEMB-UHFFFAOYSA-N 0.000 description 1
- AUYJMVMBVRSCMW-UHFFFAOYSA-N 5-nitro-1,2-benzothiazole Chemical compound [O-][N+](=O)C1=CC=C2SN=CC2=C1 AUYJMVMBVRSCMW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- GHDIHPNJQVDFBL-UHFFFAOYSA-N methoxycyclohexane Chemical compound COC1CCCCC1 GHDIHPNJQVDFBL-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2609864A DE2609864C2 (de) | 1976-03-10 | 1976-03-10 | Verfahren zur Herstellung von 3-Amino-1,2-benzisothiazolen |
| US05/768,051 US4140692A (en) | 1976-03-10 | 1977-02-14 | Manufacture of 3-amino-1,2-benzisothiazoles |
| BE174943A BE851439A (fr) | 1976-03-10 | 1977-02-15 | Procede de preparation de 3-amino-1,2-benzisothiazoles |
| FR7706042A FR2343734A1 (fr) | 1976-03-10 | 1977-03-02 | Procede de preparation de 3-amino-1,2-benzisothiazoles |
| GB9847/77A GB1571952A (en) | 1976-03-10 | 1977-03-09 | 3-amino-1,2-benzisothiazol and manufacture of 3-amino-1,2-benzisothiazoles |
| CH296677A CH626078A5 (enExample) | 1976-03-10 | 1977-03-09 | |
| JP2553277A JPS52108971A (en) | 1976-03-10 | 1977-03-10 | Production of 33aminoo1*22 benzoisothiazol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2609864A DE2609864C2 (de) | 1976-03-10 | 1976-03-10 | Verfahren zur Herstellung von 3-Amino-1,2-benzisothiazolen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2609864A1 DE2609864A1 (de) | 1977-09-15 |
| DE2609864C2 true DE2609864C2 (de) | 1984-02-16 |
Family
ID=5971984
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2609864A Expired DE2609864C2 (de) | 1976-03-10 | 1976-03-10 | Verfahren zur Herstellung von 3-Amino-1,2-benzisothiazolen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4140692A (enExample) |
| JP (1) | JPS52108971A (enExample) |
| BE (1) | BE851439A (enExample) |
| CH (1) | CH626078A5 (enExample) |
| DE (1) | DE2609864C2 (enExample) |
| FR (1) | FR2343734A1 (enExample) |
| GB (1) | GB1571952A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2734866A1 (de) * | 1977-08-03 | 1979-02-22 | Basf Ag | Neue 1,2-benzisothiazole und verfahren zu ihrer herstellung |
| JP3701044B2 (ja) * | 1995-04-24 | 2005-09-28 | 住友精化株式会社 | シアノベンゼンスルフェニルハライドおよびそれを用いる３−置換ベンゾイソチアゾールの製造方法 |
| WO2013014665A1 (en) | 2011-07-28 | 2013-01-31 | Mapi Pharma Ltd. | Intermediate compounds and process for the preparation of lurasidone and salts thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3254094A (en) * | 1964-10-20 | 1966-05-31 | Smith Kline French Lab | 3-imino-2, 1-benzisothiazoles |
| US3682941A (en) * | 1967-03-18 | 1972-08-08 | Basf Ag | Production of 1,2-benzoisothiazoles |
| DE1670907B2 (de) * | 1967-08-16 | 1976-07-22 | Bayer Ag, 5090 Leverkusen | N-disubstituierte 3-amino-1,2benzisothiazole und verfahren in ihrer herstellung |
-
1976
- 1976-03-10 DE DE2609864A patent/DE2609864C2/de not_active Expired
-
1977
- 1977-02-14 US US05/768,051 patent/US4140692A/en not_active Expired - Lifetime
- 1977-02-15 BE BE174943A patent/BE851439A/xx not_active IP Right Cessation
- 1977-03-02 FR FR7706042A patent/FR2343734A1/fr active Granted
- 1977-03-09 GB GB9847/77A patent/GB1571952A/en not_active Expired
- 1977-03-09 CH CH296677A patent/CH626078A5/de not_active IP Right Cessation
- 1977-03-10 JP JP2553277A patent/JPS52108971A/ja active Pending
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| CH626078A5 (enExample) | 1981-10-30 |
| DE2609864A1 (de) | 1977-09-15 |
| US4140692A (en) | 1979-02-20 |
| BE851439A (fr) | 1977-08-16 |
| FR2343734A1 (fr) | 1977-10-07 |
| JPS52108971A (en) | 1977-09-12 |
| FR2343734B3 (enExample) | 1980-12-19 |
| GB1571952A (en) | 1980-07-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |