TW408118B - A process for making 2-(methylthio)-5-(trifluoromethyl)-1, 3, 4-thiadiazole using methyldithiocarbazinate - Google Patents
A process for making 2-(methylthio)-5-(trifluoromethyl)-1, 3, 4-thiadiazole using methyldithiocarbazinate Download PDFInfo
- Publication number
- TW408118B TW408118B TW087120570A TW87120570A TW408118B TW 408118 B TW408118 B TW 408118B TW 087120570 A TW087120570 A TW 087120570A TW 87120570 A TW87120570 A TW 87120570A TW 408118 B TW408118 B TW 408118B
- Authority
- TW
- Taiwan
- Prior art keywords
- patent application
- acid
- item
- bis
- thiadiazole
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 50
- ULROOIOMHZXHRY-UHFFFAOYSA-N 2-methylsulfanyl-5-(trifluoromethyl)-1,3,4-thiadiazole Chemical compound CSC1=NN=C(C(F)(F)F)S1 ULROOIOMHZXHRY-UHFFFAOYSA-N 0.000 title abstract description 4
- 230000008569 process Effects 0.000 title abstract description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract description 114
- 239000000203 mixture Substances 0.000 claims abstract description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 64
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 238000011049 filling Methods 0.000 claims description 12
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 230000002079 cooperative effect Effects 0.000 claims description 8
- 239000006184 cosolvent Substances 0.000 claims description 8
- -1 2,5-bis- (fluorenylthio) -1,3,4-thiadiazole Chemical compound 0.000 claims description 7
- 150000007522 mineralic acids Chemical class 0.000 claims description 7
- 230000020477 pH reduction Effects 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 5
- 229910017604 nitric acid Inorganic materials 0.000 claims description 5
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 5
- 238000005191 phase separation Methods 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- XDDZFJKRBGYRAK-UHFFFAOYSA-N CSC=1SC(=NN1)C1=C(C(=C(C=2C3=CC=CC=C3CC12)F)F)F Chemical compound CSC=1SC(=NN1)C1=C(C(=C(C=2C3=CC=CC=C3CC12)F)F)F XDDZFJKRBGYRAK-UHFFFAOYSA-N 0.000 claims 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 2
- IUVACELPFXBLHY-UHFFFAOYSA-N 2,5-bis(methylsulfanyl)-1,3,4-thiadiazole Chemical compound CSC1=NN=C(SC)S1 IUVACELPFXBLHY-UHFFFAOYSA-N 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 62
- 239000006227 byproduct Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000376 reactant Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000015170 shellfish Nutrition 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- LOWDTDFDQBXBNR-UHFFFAOYSA-N [H]C([H])([H])SSNN Chemical compound [H]C([H])([H])SSNN LOWDTDFDQBXBNR-UHFFFAOYSA-N 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
- 238000011005 laboratory method Methods 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- FBSFWRHWHYMIOG-UHFFFAOYSA-N methyl 3,4,5-trihydroxybenzoate Chemical compound COC(=O)C1=CC(O)=C(O)C(O)=C1 FBSFWRHWHYMIOG-UHFFFAOYSA-N 0.000 description 2
- 231100000989 no adverse effect Toxicity 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 1
- XBGRMKUFDAGJDV-UHFFFAOYSA-N 2,2,2-trifluoroethanimidamide;hydrochloride Chemical compound Cl.NC(=N)C(F)(F)F XBGRMKUFDAGJDV-UHFFFAOYSA-N 0.000 description 1
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CCXSQTZLVSYCCX-UHFFFAOYSA-N C1(=CC=CC=2C3=CC=CC=C3CC12)C(=S)SC Chemical compound C1(=CC=CC=2C3=CC=CC=C3CC12)C(=S)SC CCXSQTZLVSYCCX-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- DPFFXSPEODLYOH-UHFFFAOYSA-N bis($l^{1}-oxidanyl)methanone Chemical compound [O]C([O])=O DPFFXSPEODLYOH-UHFFFAOYSA-N 0.000 description 1
- JRFLQUPXMGBBNQ-UHFFFAOYSA-N carbamodithioic acid;hydrazine Chemical compound NN.NC(S)=S JRFLQUPXMGBBNQ-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000003179 convulsant agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- IBKQQKPQRYUGBJ-UHFFFAOYSA-N methyl gallate Natural products CC(=O)C1=CC(O)=C(O)C(O)=C1 IBKQQKPQRYUGBJ-UHFFFAOYSA-N 0.000 description 1
- WFJRIDQGVSJLLH-UHFFFAOYSA-N methyl n-aminocarbamate Chemical compound COC(=O)NN WFJRIDQGVSJLLH-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Substances FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/989,563 US6005114A (en) | 1997-12-12 | 1997-12-12 | Process for making 2-(methylthio)-5(trifluoromethyl)-1,3,4,-thiadiazole using methyldithiocarbazinate with trifluoroacetic acid with selective removal of 2,5-bis(methylthio)-1,3,4-thiadiazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW408118B true TW408118B (en) | 2000-10-11 |
Family
ID=25535229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW087120570A TW408118B (en) | 1997-12-12 | 1998-12-11 | A process for making 2-(methylthio)-5-(trifluoromethyl)-1, 3, 4-thiadiazole using methyldithiocarbazinate |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US6005114A (en, 2012) |
| EP (1) | EP0926141B1 (en, 2012) |
| JP (1) | JP4497568B2 (en, 2012) |
| KR (1) | KR100577635B1 (en, 2012) |
| CN (1) | CN1117739C (en, 2012) |
| BR (1) | BR9805393B1 (en, 2012) |
| CA (1) | CA2254610C (en, 2012) |
| DE (1) | DE69834471T2 (en, 2012) |
| DK (1) | DK0926141T3 (en, 2012) |
| ES (1) | ES2258808T3 (en, 2012) |
| HU (1) | HU221653B1 (en, 2012) |
| IL (1) | IL127457A (en, 2012) |
| IN (1) | IN191508B (en, 2012) |
| TW (1) | TW408118B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6469175B1 (en) | 2001-02-20 | 2002-10-22 | Bayer Corporation | Methods of purifying 2-methylthio-5-trifluoromethyl-1,3,4-thiadiazole |
| RU2455294C2 (ru) * | 2010-01-11 | 2012-07-10 | Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран | Способ получения 2,5-диалкил-3-фенил(бензил)-1,3,4-тиадиазолидинов |
| CN104119296A (zh) * | 2013-04-25 | 2014-10-29 | 苏州科捷生物医药有限公司 | 一种2-三氟甲基-5-哌嗪基-噻二唑的合成方法 |
| CN105646397A (zh) * | 2014-11-27 | 2016-06-08 | 孙智华 | 一种氟噻草胺的制备方法 |
| EP3415506A1 (en) | 2017-06-13 | 2018-12-19 | Solvay Sa | Process for the manufacture of haloalkyl substituted thiadiazole compounds |
| CN111925340A (zh) * | 2019-12-16 | 2020-11-13 | 山东金城柯瑞化学有限公司 | 一种甲基巯基噻二唑的制备工艺 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3562284A (en) * | 1968-02-05 | 1971-02-09 | American Cyanamid Co | 2-(substituted) sulfonyl-5-trifluoromethyl-1,3,4-thiadiazoles |
| DE3422861A1 (de) * | 1984-06-20 | 1986-01-02 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von heteroaryloxyacetamiden |
| DE3722320A1 (de) * | 1987-07-07 | 1989-01-19 | Bayer Ag | Mikrobizide mittel |
| US5177090A (en) * | 1987-07-07 | 1993-01-05 | Bayer Aktiengesellschaft | Microbicidal agents |
| DE3821597A1 (de) * | 1988-06-27 | 1989-12-28 | Bayer Ag | 5-difluormethyl-1,3,4-thiadiazol-2-yl- oxyessigsaeureamide, verfahren und 5-difluormethyl-2- methylsulfonyl- bzw. 2- methylthio-1,3,4-thiadiazol als zwischenprodukte zu ihrer herstellung und ihre verwendung als selektivherbizide |
| DE4003436A1 (de) * | 1990-02-06 | 1991-08-08 | Bayer Ag | Verfahren zur herstellung von 2-alkylthio-1,3,4-thiadiazolen |
-
1997
- 1997-12-12 US US08/989,563 patent/US6005114A/en not_active Expired - Lifetime
-
1998
- 1998-11-27 CA CA002254610A patent/CA2254610C/en not_active Expired - Lifetime
- 1998-12-01 DK DK98122760T patent/DK0926141T3/da active
- 1998-12-01 EP EP98122760A patent/EP0926141B1/en not_active Expired - Lifetime
- 1998-12-01 ES ES98122760T patent/ES2258808T3/es not_active Expired - Lifetime
- 1998-12-01 DE DE69834471T patent/DE69834471T2/de not_active Expired - Lifetime
- 1998-12-02 KR KR1019980052634A patent/KR100577635B1/ko not_active Expired - Lifetime
- 1998-12-09 IN IN3709DE1998 patent/IN191508B/en unknown
- 1998-12-09 JP JP34996398A patent/JP4497568B2/ja not_active Expired - Lifetime
- 1998-12-09 IL IL12745798A patent/IL127457A/en not_active IP Right Cessation
- 1998-12-10 HU HU9802874A patent/HU221653B1/hu not_active IP Right Cessation
- 1998-12-11 TW TW087120570A patent/TW408118B/zh not_active IP Right Cessation
- 1998-12-11 BR BRPI9805393-0A patent/BR9805393B1/pt not_active IP Right Cessation
- 1998-12-11 CN CN98125307A patent/CN1117739C/zh not_active Expired - Lifetime
- 1998-12-18 US US09/215,492 patent/US6034245A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CN1117739C (zh) | 2003-08-13 |
| HK1020733A1 (en) | 2000-05-19 |
| US6034245A (en) | 2000-03-07 |
| HU9802874D0 (en) | 1999-02-01 |
| HU221653B1 (hu) | 2002-12-28 |
| IL127457A0 (en) | 1999-10-28 |
| EP0926141B1 (en) | 2006-05-10 |
| CA2254610C (en) | 2008-10-14 |
| US6005114A (en) | 1999-12-21 |
| HUP9802874A2 (hu) | 1999-09-28 |
| ES2258808T3 (es) | 2006-09-01 |
| HUP9802874A3 (en) | 2000-02-28 |
| IN191508B (en, 2012) | 2003-12-06 |
| IL127457A (en) | 2001-09-13 |
| EP0926141A1 (en) | 1999-06-30 |
| KR100577635B1 (ko) | 2006-09-27 |
| DE69834471D1 (de) | 2006-06-14 |
| CN1221740A (zh) | 1999-07-07 |
| DK0926141T3 (da) | 2006-09-11 |
| BR9805393B1 (pt) | 2009-08-11 |
| BR9805393A (pt) | 2000-02-01 |
| CA2254610A1 (en) | 1999-06-12 |
| KR19990062740A (ko) | 1999-07-26 |
| DE69834471T2 (de) | 2006-12-14 |
| JP4497568B2 (ja) | 2010-07-07 |
| JPH11236380A (ja) | 1999-08-31 |
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