DK3166404T3 - Forbedret fremgangsmåde til fremstilling af 4-(1-(4-(perfluoroethoxy)phenyl)-1h-1,2,4-triazo-3-yl)benzoylazid - Google Patents
Forbedret fremgangsmåde til fremstilling af 4-(1-(4-(perfluoroethoxy)phenyl)-1h-1,2,4-triazo-3-yl)benzoylazid Download PDFInfo
- Publication number
- DK3166404T3 DK3166404T3 DK15818742.7T DK15818742T DK3166404T3 DK 3166404 T3 DK3166404 T3 DK 3166404T3 DK 15818742 T DK15818742 T DK 15818742T DK 3166404 T3 DK3166404 T3 DK 3166404T3
- Authority
- DK
- Denmark
- Prior art keywords
- triaryl
- formula
- phenyl
- perfluoroethoxy
- organic solvent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- -1 4- (PERFLUOROETHOXY) PHENYL Chemical class 0.000 title description 12
- PJHUABJTDFXYRQ-UHFFFAOYSA-N benzoyl azide Chemical compound [N-]=[N+]=NC(=O)C1=CC=CC=C1 PJHUABJTDFXYRQ-UHFFFAOYSA-N 0.000 title description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 150000008064 anhydrides Chemical class 0.000 claims description 12
- 239000002585 base Substances 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 7
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 150000001540 azides Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000004438 haloalkoxy group Chemical group 0.000 description 6
- 125000001188 haloalkyl group Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000152 carbamate pesticide Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CELWCAITJAEQNL-UHFFFAOYSA-N oxan-2-ol Chemical compound OC1CCCCO1 CELWCAITJAEQNL-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-nitrogen bonds, e.g. azides, diazo-amino compounds, diazonium compounds, hydrazine derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (4)
1. Fremgangsmåde til fremstilling af visse triarylacylazider med formlen (I),
hvori Ri repræsenterer (Ci-Ce)-halogenalkyl eller (Ci-C6)-halogenalkoxy, hvilken fremgangsmåde omfatter a) at kontakte en triarylsyre med formel (II)
hvori Ri er som tidligere defineret, med chlorcarbonat med formel (IV)
hvori R2 repræsenterer (Ci-C6)-alkyl, phenyl eller benzyl, i nærvær afen base i et organisk opløsningsmiddel, der er tetrahydrofuran eller dimethoxy-ethan, for at tilvejebringe et triarylblandet anhydrid med formel (V)
hvori Ri og R2 er som tidligere defineret, og
b) at bringe triarylblandet anhydrid med formel (V) i kontakt med en vandig opløsning af natriumazid i det organiske opløsningsmiddel tetrahy-drofuran eller dimethoxyethan.
2. Fremgangsmåden ifølge krav 1, hvori Ri er OCF2CF3.
3. Fremgangsmåden ifølge krav 1, hvori R2 er CH2CH3.
4. Fremgangsmåden ifølge krav 1, hvor basen er et alkalimetalcarbonat, en tertiær amin eller en aromatisk amin.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462023225P | 2014-07-11 | 2014-07-11 | |
| PCT/US2015/039713 WO2016007726A1 (en) | 2014-07-11 | 2015-07-09 | Improved process for preparation of 4-(1-(4-(perfluoroethoxy)phenyl)-1h-1,2,4-triazol-3-yl)benzoyl azide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK3166404T3 true DK3166404T3 (da) | 2019-04-01 |
Family
ID=55064886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK15818742.7T DK3166404T3 (da) | 2014-07-11 | 2015-07-09 | Forbedret fremgangsmåde til fremstilling af 4-(1-(4-(perfluoroethoxy)phenyl)-1h-1,2,4-triazo-3-yl)benzoylazid |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9796689B2 (da) |
| EP (1) | EP3166404B1 (da) |
| JP (1) | JP6585634B2 (da) |
| KR (1) | KR102468066B1 (da) |
| CN (1) | CN106659155B (da) |
| AR (1) | AR101183A1 (da) |
| BR (1) | BR112016029043B8 (da) |
| CA (1) | CA2952049C (da) |
| DK (1) | DK3166404T3 (da) |
| ES (1) | ES2717148T3 (da) |
| IL (1) | IL249496B (da) |
| MX (1) | MX377787B (da) |
| TW (1) | TWI653227B (da) |
| WO (1) | WO2016007726A1 (da) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5736528A (en) * | 1993-10-28 | 1998-04-07 | University Of Florida Research Foundation, Inc. | N6 -(epoxynorborn-2-yl) adenosines as A1 adenosine receptor agonists |
| GB0322016D0 (en) * | 2003-09-19 | 2003-10-22 | Merck Sharp & Dohme | New compounds |
| US7226951B2 (en) * | 2003-12-17 | 2007-06-05 | Allergan, Inc. | Compounds having selective cytochrome P450RAI-1 or selective cytochrome P450RAI-2 inhibitory activity and methods of obtaining the same |
| US7572805B2 (en) * | 2004-07-14 | 2009-08-11 | Bristol-Myers Squibb Company | Pyrrolo(oxo)isoquinolines as 5HT ligands |
| NZ587143A (en) * | 2008-02-12 | 2011-07-29 | Dow Agrosciences Llc | Pesticidal compositions |
| KR101798248B1 (ko) * | 2009-08-07 | 2017-11-15 | 다우 아그로사이언시즈 엘엘씨 | 살충 조성물 |
-
2015
- 2015-06-24 TW TW104120318A patent/TWI653227B/zh not_active IP Right Cessation
- 2015-07-09 EP EP15818742.7A patent/EP3166404B1/en active Active
- 2015-07-09 WO PCT/US2015/039713 patent/WO2016007726A1/en not_active Ceased
- 2015-07-09 KR KR1020167034711A patent/KR102468066B1/ko active Active
- 2015-07-09 DK DK15818742.7T patent/DK3166404T3/da active
- 2015-07-09 JP JP2016572811A patent/JP6585634B2/ja not_active Expired - Fee Related
- 2015-07-09 CN CN201580031318.9A patent/CN106659155B/zh not_active Expired - Fee Related
- 2015-07-09 ES ES15818742T patent/ES2717148T3/es active Active
- 2015-07-09 CA CA2952049A patent/CA2952049C/en active Active
- 2015-07-09 BR BR112016029043A patent/BR112016029043B8/pt not_active IP Right Cessation
- 2015-07-09 MX MX2016016302A patent/MX377787B/es active IP Right Grant
- 2015-07-09 US US14/795,319 patent/US9796689B2/en not_active Expired - Fee Related
- 2015-07-10 AR ARP150102210A patent/AR101183A1/es active IP Right Grant
-
2016
- 2016-12-11 IL IL249496A patent/IL249496B/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| WO2016007726A1 (en) | 2016-01-14 |
| EP3166404A1 (en) | 2017-05-17 |
| MX2016016302A (es) | 2017-03-31 |
| US9796689B2 (en) | 2017-10-24 |
| TW201625562A (zh) | 2016-07-16 |
| BR112016029043A8 (pt) | 2021-03-23 |
| CN106659155B (zh) | 2019-09-24 |
| KR20170029421A (ko) | 2017-03-15 |
| CA2952049C (en) | 2022-06-07 |
| CN106659155A (zh) | 2017-05-10 |
| KR102468066B1 (ko) | 2022-11-17 |
| EP3166404B1 (en) | 2018-12-26 |
| BR112016029043B8 (pt) | 2022-08-23 |
| CA2952049A1 (en) | 2016-01-14 |
| ES2717148T3 (es) | 2019-06-19 |
| BR112016029043B1 (pt) | 2021-08-17 |
| AR101183A1 (es) | 2016-11-30 |
| IL249496A0 (en) | 2017-02-28 |
| EP3166404A4 (en) | 2018-01-10 |
| IL249496B (en) | 2019-12-31 |
| JP2017521391A (ja) | 2017-08-03 |
| BR112016029043A2 (pt) | 2017-08-22 |
| US20160009665A1 (en) | 2016-01-14 |
| TWI653227B (zh) | 2019-03-11 |
| JP6585634B2 (ja) | 2019-10-02 |
| MX377787B (es) | 2025-03-11 |
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