ZA200209476B - Method for producing 2-chloro-5-chloromethyl-1,3-thiazole. - Google Patents
Method for producing 2-chloro-5-chloromethyl-1,3-thiazole. Download PDFInfo
- Publication number
- ZA200209476B ZA200209476B ZA200209476A ZA200209476A ZA200209476B ZA 200209476 B ZA200209476 B ZA 200209476B ZA 200209476 A ZA200209476 A ZA 200209476A ZA 200209476 A ZA200209476 A ZA 200209476A ZA 200209476 B ZA200209476 B ZA 200209476B
- Authority
- ZA
- South Africa
- Prior art keywords
- chloro
- process according
- thiazole
- chloromethyl
- mol
- Prior art date
Links
- VRMUIVKEHJSADG-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)-1,3-thiazole Chemical compound ClCC1=CN=C(Cl)S1 VRMUIVKEHJSADG-UHFFFAOYSA-N 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title description 2
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 claims description 46
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 42
- 235000016720 allyl isothiocyanate Nutrition 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 238000009835 boiling Methods 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000007800 oxidant agent Substances 0.000 claims description 14
- 239000013078 crystal Substances 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 11
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 11
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 10
- 239000012320 chlorinating reagent Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 8
- 230000002140 halogenating effect Effects 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 7
- 238000002425 crystallisation Methods 0.000 claims description 7
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- 229960002317 succinimide Drugs 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- 229960001701 chloroform Drugs 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000003999 initiator Substances 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- MARXMDRWROUXMD-UHFFFAOYSA-N 2-bromoisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(Br)C(=O)C2=C1 MARXMDRWROUXMD-UHFFFAOYSA-N 0.000 claims description 3
- WDRFYIPWHMGQPN-UHFFFAOYSA-N 2-chloroisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(Cl)C(=O)C2=C1 WDRFYIPWHMGQPN-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000004816 dichlorobenzenes Chemical class 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 150000001451 organic peroxides Chemical class 0.000 claims description 2
- 150000004965 peroxy acids Chemical class 0.000 claims description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-Chlorosuccinimide Substances ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 24
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 230000029087 digestion Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- -1 nickel peroxide Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UOORRWUZONOOLO-OWOJBTEDSA-N (E)-1,3-dichloropropene Chemical compound ClC\C=C\Cl UOORRWUZONOOLO-OWOJBTEDSA-N 0.000 description 1
- NYFSGZTZZAYKQO-HNQUOIGGSA-N (e)-3-chloro-1-isothiocyanatoprop-1-ene Chemical compound ClC\C=C\N=C=S NYFSGZTZZAYKQO-HNQUOIGGSA-N 0.000 description 1
- DGBFPSVUFUDQNA-UHFFFAOYSA-N 2-chloro-3-isothiocyanatoprop-1-ene Chemical compound ClC(=C)CN=C=S DGBFPSVUFUDQNA-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- GUABFMPMKJGSBQ-UHFFFAOYSA-N 5-methyl-1,3-thiazol-2-amine Chemical compound CC1=CN=C(N)S1 GUABFMPMKJGSBQ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- UOORRWUZONOOLO-UHFFFAOYSA-N telone II Natural products ClCC=CCl UOORRWUZONOOLO-UHFFFAOYSA-N 0.000 description 1
- 150000003567 thiocyanates Chemical class 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
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0089500A AT408756B (de) | 2000-05-23 | 2000-05-23 | Verfahren zur herstellung von 2-chlor-5-chlormethyl-1,3-thiazol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200209476B true ZA200209476B (en) | 2003-07-23 |
Family
ID=3682855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200209476A ZA200209476B (en) | 2000-05-23 | 2002-11-21 | Method for producing 2-chloro-5-chloromethyl-1,3-thiazole. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6787654B2 (he) |
| EP (1) | EP1286976B1 (he) |
| JP (1) | JP2003534335A (he) |
| KR (1) | KR100780564B1 (he) |
| CN (1) | CN1190429C (he) |
| AT (2) | AT408756B (he) |
| AU (2) | AU2001268981B2 (he) |
| BR (1) | BR0111039B1 (he) |
| CA (1) | CA2408135C (he) |
| CZ (1) | CZ301567B6 (he) |
| DE (1) | DE50115814D1 (he) |
| HU (1) | HUP0301893A3 (he) |
| IL (2) | IL152704A0 (he) |
| MX (1) | MXPA02011312A (he) |
| PL (1) | PL358329A1 (he) |
| RU (1) | RU2002133097A (he) |
| WO (1) | WO2001090089A1 (he) |
| ZA (1) | ZA200209476B (he) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE602005026107D1 (de) * | 2004-03-22 | 2011-03-10 | Sumitomo Chemical Co | Verfahren zur aufreinigung von 2-chlor-5-chlormethyl-1,3-thiazol |
| JP5066808B2 (ja) | 2006-01-13 | 2012-11-07 | 住友化学株式会社 | チアゾール化合物の製造方法 |
| CN103755661B (zh) * | 2014-02-08 | 2016-09-21 | 山东省农药科学研究院 | 一种2-氯-5-氯甲基噻唑的分离精制方法 |
| CN103739567B (zh) * | 2014-02-08 | 2016-09-21 | 山东省农药科学研究院 | 一种2-氯-5-氯甲基噻唑晶型及制备方法 |
| AR114185A1 (es) * | 2018-01-23 | 2020-07-29 | Adama Makhteshim Ltd | Síntesis de 5-cloro-2-[(3,4,4-trifluoro-3-buten-1-il)tio]-tiazol |
| CN112661717B (zh) * | 2020-12-30 | 2022-10-18 | 邯郸市瑞田农药有限公司 | 2-氯-5-氯甲基噻唑光催化氯化的合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3631538A1 (de) * | 1986-09-17 | 1988-03-24 | Bayer Ag | Verfahren zur herstellung von 2-chlor-5-chlormethylthiazol |
| US5180833A (en) * | 1990-03-16 | 1993-01-19 | Takeda Chemical Industries, Ltd. | Process for the preparation of chlorothiazole derivatives |
| GB9518824D0 (en) * | 1995-09-14 | 1995-11-15 | Fine Organics Ltd | Preparation of substituted thiazoles |
| US5811555A (en) * | 1995-11-22 | 1998-09-22 | Kureha Chemical Industry Co., Ltd. | Method for substitution of an amino group of a primary amine by a chlorine atom and a synthetic method by application thereof |
| IN182219B (he) * | 1996-02-21 | 1999-02-06 | Kuraray Co | |
| DE19908447A1 (de) * | 1999-02-26 | 2000-08-31 | Bayer Ag | Verfahren zur Herstellung von 2-Chlor-5-chlormethylthiazol |
-
2000
- 2000-05-23 AT AT0089500A patent/AT408756B/de not_active IP Right Cessation
-
2001
- 2001-04-26 AU AU2001268981A patent/AU2001268981B2/en not_active Ceased
- 2001-04-26 EP EP01947242A patent/EP1286976B1/de not_active Expired - Lifetime
- 2001-04-26 AT AT01947242T patent/ATE501129T1/de active
- 2001-04-26 JP JP2001586277A patent/JP2003534335A/ja active Pending
- 2001-04-26 DE DE50115814T patent/DE50115814D1/de not_active Expired - Lifetime
- 2001-04-26 AU AU6898101A patent/AU6898101A/xx active Pending
- 2001-04-26 US US10/296,488 patent/US6787654B2/en not_active Expired - Fee Related
- 2001-04-26 BR BRPI0111039-0A patent/BR0111039B1/pt not_active IP Right Cessation
- 2001-04-26 HU HU0301893A patent/HUP0301893A3/hu unknown
- 2001-04-26 RU RU2002133097/04A patent/RU2002133097A/ru not_active Application Discontinuation
- 2001-04-26 PL PL01358329A patent/PL358329A1/xx not_active Application Discontinuation
- 2001-04-26 CA CA002408135A patent/CA2408135C/en not_active Expired - Fee Related
- 2001-04-26 IL IL15270401A patent/IL152704A0/xx active IP Right Grant
- 2001-04-26 KR KR1020027015722A patent/KR100780564B1/ko not_active IP Right Cessation
- 2001-04-26 CZ CZ20023843A patent/CZ301567B6/cs not_active IP Right Cessation
- 2001-04-26 MX MXPA02011312A patent/MXPA02011312A/es unknown
- 2001-04-26 CN CNB018099726A patent/CN1190429C/zh not_active Expired - Fee Related
- 2001-04-26 WO PCT/EP2001/004693 patent/WO2001090089A1/de active IP Right Grant
-
2002
- 2002-11-07 IL IL152704A patent/IL152704A/he not_active IP Right Cessation
- 2002-11-21 ZA ZA200209476A patent/ZA200209476B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR100780564B1 (ko) | 2007-11-29 |
| EP1286976B1 (de) | 2011-03-09 |
| BR0111039B1 (pt) | 2013-01-22 |
| DE50115814D1 (de) | 2011-04-21 |
| IL152704A (he) | 2008-11-26 |
| WO2001090089A1 (de) | 2001-11-29 |
| BR0111039A (pt) | 2003-04-08 |
| AT408756B (de) | 2002-03-25 |
| US6787654B2 (en) | 2004-09-07 |
| ATE501129T1 (de) | 2011-03-15 |
| EP1286976A1 (de) | 2003-03-05 |
| CZ20023843A3 (cs) | 2003-05-14 |
| CA2408135A1 (en) | 2001-11-29 |
| US20030153767A1 (en) | 2003-08-14 |
| MXPA02011312A (es) | 2005-09-08 |
| KR20030003748A (ko) | 2003-01-10 |
| CN1190429C (zh) | 2005-02-23 |
| JP2003534335A (ja) | 2003-11-18 |
| RU2002133097A (ru) | 2004-09-20 |
| HUP0301893A2 (hu) | 2003-09-29 |
| CN1430613A (zh) | 2003-07-16 |
| HUP0301893A3 (en) | 2005-11-28 |
| CZ301567B6 (cs) | 2010-04-21 |
| IL152704A0 (en) | 2003-06-24 |
| PL358329A1 (en) | 2004-08-09 |
| CA2408135C (en) | 2009-10-20 |
| AU6898101A (en) | 2001-12-03 |
| ATA8952000A (de) | 2001-07-15 |
| AU2001268981B2 (en) | 2004-11-04 |
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