AU2001287117B2 - Process to produce halo-4-phenoxyquinolines - Google Patents
Process to produce halo-4-phenoxyquinolines Download PDFInfo
- Publication number
- AU2001287117B2 AU2001287117B2 AU2001287117A AU2001287117A AU2001287117B2 AU 2001287117 B2 AU2001287117 B2 AU 2001287117B2 AU 2001287117 A AU2001287117 A AU 2001287117A AU 2001287117 A AU2001287117 A AU 2001287117A AU 2001287117 B2 AU2001287117 B2 AU 2001287117B2
- Authority
- AU
- Australia
- Prior art keywords
- compound
- formula
- halo
- alkyl
- produce
- 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
- 238000000034 method Methods 0.000 title claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims description 116
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 17
- -1 phenoxy, substituted phenoxy, phenylthio, substituted phenylthio Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 239000000295 fuel oil Substances 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 claims description 2
- 101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 claims 1
- 102100029645 UBX domain-containing protein 11 Human genes 0.000 claims 1
- DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical group ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 239000000417 fungicide Substances 0.000 description 7
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 3
- DJJDCKKEHWFLMK-UHFFFAOYSA-N 5,7-dichloro-2-fluoro-4-phenoxyquinoline Chemical compound C=12C(Cl)=CC(Cl)=CC2=NC(F)=CC=1OC1=CC=CC=C1 DJJDCKKEHWFLMK-UHFFFAOYSA-N 0.000 description 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- OVAXVANZWJUQBI-UHFFFAOYSA-N 2,3,4-trichloroquinoline Chemical class C1=CC=C2C(Cl)=C(Cl)C(Cl)=NC2=C1 OVAXVANZWJUQBI-UHFFFAOYSA-N 0.000 description 2
- XOJXGDQMNWRRTP-UHFFFAOYSA-N 3,5-dichloro-1h-quinolin-4-one Chemical compound C1=CC(Cl)=C2C(O)=C(Cl)C=NC2=C1 XOJXGDQMNWRRTP-UHFFFAOYSA-N 0.000 description 2
- UQRLKWGPEVNVHT-UHFFFAOYSA-N 3,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1 UQRLKWGPEVNVHT-UHFFFAOYSA-N 0.000 description 2
- WWFMSYKATMDLJP-UHFFFAOYSA-N 4,5,7-trichloroquinoline Chemical compound ClC1=CC=NC2=CC(Cl)=CC(Cl)=C21 WWFMSYKATMDLJP-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- GLRWPJIYVQVSTJ-UHFFFAOYSA-N ClC1(CN=C2C=CC=C(C2=C1O)Cl)C(=O)O Chemical compound ClC1(CN=C2C=CC=C(C2=C1O)Cl)C(=O)O GLRWPJIYVQVSTJ-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23171900P | 2000-09-08 | 2000-09-08 | |
| US60/231,719 | 2000-09-08 | ||
| PCT/US2001/027689 WO2002020490A2 (en) | 2000-09-08 | 2001-09-07 | Process to produce halo-4-phenoxyquinolines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2001287117A1 AU2001287117A1 (en) | 2002-06-13 |
| AU2001287117B2 true AU2001287117B2 (en) | 2007-09-06 |
Family
ID=22870393
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2001287117A Expired AU2001287117B2 (en) | 2000-09-08 | 2001-09-07 | Process to produce halo-4-phenoxyquinolines |
| AU8711701A Pending AU8711701A (en) | 2000-09-08 | 2001-09-07 | Process to produce halo-4-phenoxyquinolines |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU8711701A Pending AU8711701A (en) | 2000-09-08 | 2001-09-07 | Process to produce halo-4-phenoxyquinolines |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1315702B1 (enExample) |
| JP (1) | JP5761886B2 (enExample) |
| KR (1) | KR100796181B1 (enExample) |
| CN (1) | CN1268613C (enExample) |
| AT (1) | ATE282026T1 (enExample) |
| AU (2) | AU2001287117B2 (enExample) |
| BR (1) | BRPI0113727B8 (enExample) |
| DE (1) | DE60107098T2 (enExample) |
| DK (1) | DK1315702T3 (enExample) |
| HU (1) | HU230651B1 (enExample) |
| IL (2) | IL154764A0 (enExample) |
| WO (1) | WO2002020490A2 (enExample) |
| ZA (1) | ZA200302088B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH076406B2 (ja) | 1986-07-09 | 1995-01-30 | 株式会社東芝 | ガスタ−ビン用減温器 |
| CN108689927B (zh) * | 2018-07-09 | 2020-07-03 | 陕西恒润化学工业有限公司 | 一种苯氧喹啉及其合成方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998033774A1 (en) * | 1997-01-31 | 1998-08-06 | Dow Agrosciences Llc | Improved process for the preparation of halo-4-phenoxyquinolines |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5245036A (en) * | 1992-05-07 | 1993-09-14 | Dowelanco | Process for the preparation of 4-phenoxyquinoline compounds |
| CH685560A5 (de) * | 1993-12-07 | 1995-08-15 | Lonza Ag | Verfahren zur Herstellung von 4-Hydroxychinolinen. |
| DE69528160T2 (de) * | 1994-03-01 | 2003-02-06 | Chemipro Kasei Kaisha, Ltd. | Verfahren zur herstellung von 5,7 dichlor-4-hydroxychinolin |
| GB9709907D0 (en) * | 1997-05-15 | 1997-07-09 | Ciba Geigy Ag | Novel combinations |
-
2001
- 2001-09-07 AU AU2001287117A patent/AU2001287117B2/en not_active Expired
- 2001-09-07 AT AT01966618T patent/ATE282026T1/de active
- 2001-09-07 BR BRPI0113727A patent/BRPI0113727B8/pt not_active IP Right Cessation
- 2001-09-07 DE DE60107098T patent/DE60107098T2/de not_active Expired - Lifetime
- 2001-09-07 DK DK01966618T patent/DK1315702T3/da active
- 2001-09-07 EP EP01966618A patent/EP1315702B1/en not_active Expired - Lifetime
- 2001-09-07 KR KR1020037003457A patent/KR100796181B1/ko not_active Expired - Lifetime
- 2001-09-07 AU AU8711701A patent/AU8711701A/xx active Pending
- 2001-09-07 WO PCT/US2001/027689 patent/WO2002020490A2/en not_active Ceased
- 2001-09-07 ZA ZA200302088A patent/ZA200302088B/en unknown
- 2001-09-07 HU HU0302110A patent/HU230651B1/hu unknown
- 2001-09-07 CN CNB018174795A patent/CN1268613C/zh not_active Expired - Lifetime
- 2001-09-07 IL IL15476401A patent/IL154764A0/xx unknown
- 2001-09-07 JP JP2002525112A patent/JP5761886B2/ja not_active Expired - Lifetime
-
2003
- 2003-03-05 IL IL154764A patent/IL154764A/en active IP Right Grant
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998033774A1 (en) * | 1997-01-31 | 1998-08-06 | Dow Agrosciences Llc | Improved process for the preparation of halo-4-phenoxyquinolines |
Non-Patent Citations (1)
| Title |
|---|
| J. Med. Chem. 41, 1998, 4918-4926 ( * |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE282026T1 (de) | 2004-11-15 |
| AU8711701A (en) | 2002-03-22 |
| BR0113727A (pt) | 2003-07-22 |
| EP1315702A2 (en) | 2003-06-04 |
| CN1268613C (zh) | 2006-08-09 |
| JP5761886B2 (ja) | 2015-08-12 |
| BRPI0113727B1 (enExample) | 2012-11-13 |
| ZA200302088B (en) | 2004-03-15 |
| DE60107098D1 (de) | 2004-12-16 |
| HU230651B1 (hu) | 2017-05-29 |
| WO2002020490A2 (en) | 2002-03-14 |
| IL154764A (en) | 2009-09-22 |
| JP2004508358A (ja) | 2004-03-18 |
| CN1541204A (zh) | 2004-10-27 |
| IL154764A0 (en) | 2003-10-31 |
| KR100796181B1 (ko) | 2008-01-21 |
| DK1315702T3 (da) | 2005-03-14 |
| EP1315702B1 (en) | 2004-11-10 |
| WO2002020490A3 (en) | 2002-06-13 |
| BRPI0113727B8 (pt) | 2022-06-28 |
| HUP0302110A2 (hu) | 2003-09-29 |
| DE60107098T2 (de) | 2005-03-24 |
| KR20030036768A (ko) | 2003-05-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired | ||
| HB | Alteration of name in register |
Owner name: CORTEVA AGRISCIENCE LLC Free format text: FORMER NAME(S): DOW AGROSCIENCES LLC |