JP2001501916A - インデノ［１，２―ｅ］［１，３，４］オキサジアジンジカルボキレートの製造方法 - Google Patents
インデノ［１，２―ｅ］［１，３，４］オキサジアジンジカルボキレートの製造方法Info
- Publication number
- JP2001501916A JP2001501916A JP10508080A JP50808098A JP2001501916A JP 2001501916 A JP2001501916 A JP 2001501916A JP 10508080 A JP10508080 A JP 10508080A JP 50808098 A JP50808098 A JP 50808098A JP 2001501916 A JP2001501916 A JP 2001501916A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- acid
- distillation
- alkoxy
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- BSTHYPUZLOXKTM-UHFFFAOYSA-N 2H-oxadiazine-4,5-dicarboxylic acid Chemical compound C1=C(C(=NNO1)C(=O)O)C(=O)O BSTHYPUZLOXKTM-UHFFFAOYSA-N 0.000 title description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 42
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 238000004821 distillation Methods 0.000 claims abstract description 24
- 239000006227 byproduct Substances 0.000 claims abstract description 14
- 239000003377 acid catalyst Substances 0.000 claims abstract description 10
- 239000012442 inert solvent Substances 0.000 claims abstract description 10
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 20
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 8
- OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- JIRHAGAOHOYLNO-UHFFFAOYSA-N (3-cyclopentyloxy-4-methoxyphenyl)methanol Chemical compound COC1=CC=C(CO)C=C1OC1CCCC1 JIRHAGAOHOYLNO-UHFFFAOYSA-N 0.000 claims description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 abstract description 3
- 150000002429 hydrazines Chemical class 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000010992 reflux Methods 0.000 description 15
- 238000009835 boiling Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- -1 drazine carboxylate Chemical class 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 150000005063 oxadiazines Chemical class 0.000 description 5
- YFVYPTZIEXOAIT-UHFFFAOYSA-N 2-o-benzyl 4a-o-methyl 7-chloro-3,5-dihydroindeno[1,2-e][1,3,4]oxadiazine-2,4a-dicarboxylate Chemical compound C1OC2(C(=O)OC)CC3=CC(Cl)=CC=C3C2=NN1C(=O)OCC1=CC=CC=C1 YFVYPTZIEXOAIT-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 238000010276 construction Methods 0.000 description 4
- 239000000498 cooling water Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- RXUBZLMIGSAPEJ-UHFFFAOYSA-N benzyl n-aminocarbamate Chemical compound NNC(=O)OCC1=CC=CC=C1 RXUBZLMIGSAPEJ-UHFFFAOYSA-N 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- YQIDAIBCMPVHIB-UHFFFAOYSA-N 6-chloro-2-hydroxy-3-oxo-1H-indene-2-carboxylic acid Chemical compound ClC1=CC=C2C(=O)C(C(=O)O)(O)CC2=C1 YQIDAIBCMPVHIB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical class FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2242696P | 1996-08-05 | 1996-08-05 | |
| US60/022,426 | 1996-08-05 | ||
| PCT/US1997/013548 WO1998005656A1 (en) | 1996-08-05 | 1997-07-31 | Processes for preparing indeno[1,2-e][1,3,4]oxadiazine-dicarboxylates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2001501916A true JP2001501916A (ja) | 2001-02-13 |
Family
ID=21809536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10508080A Pending JP2001501916A (ja) | 1996-08-05 | 1997-07-31 | インデノ［１，２―ｅ］［１，３，４］オキサジアジンジカルボキレートの製造方法 |
Country Status (11)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005323518A (ja) * | 2004-05-13 | 2005-11-24 | Chikuno Shokuhin Kogyo Kk | トコトリエノール含有家禽卵 |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU4553999A (en) * | 1998-06-10 | 1999-12-30 | E.I. Du Pont De Nemours And Company | Arthropodicidal carboxanilides |
| JP4359500B2 (ja) | 2001-06-29 | 2009-11-04 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ジルコニウム触媒によるβ−ジカルボニルのヒドロキシル化 |
| ES2823760T3 (es) | 2006-09-01 | 2021-05-10 | Fmc Corp | Formulaciones para administración tópica local que contienen indoxacarb |
| CN102391261A (zh) * | 2011-10-14 | 2012-03-28 | 上海交通大学 | 一种n-取代噁二嗪类化合物及其制备方法和应用 |
| CN104262285B (zh) * | 2014-07-24 | 2016-08-17 | 浙江大学 | 农用杀虫剂茚虫威中间体的合成法 |
| CN106397351B (zh) * | 2016-08-31 | 2018-10-30 | 京博农化科技股份有限公司 | 一种茚虫威中间体的制备方法 |
| CN108997254A (zh) * | 2018-08-27 | 2018-12-14 | 湖南国发精细化工科技有限公司 | 茚并噁二嗪化合物的合成方法 |
| CN113607833B (zh) * | 2021-07-08 | 2023-10-31 | 山东京博农化科技股份有限公司 | 一种茚虫威中间体的含量分析方法 |
| CN113607836B (zh) * | 2021-07-23 | 2023-10-31 | 山东京博农化科技股份有限公司 | 一种茚虫威关键中间体含量的分析方法 |
| CN118556052A (zh) | 2022-01-04 | 2024-08-27 | 安道麦马克西姆有限公司 | 茚虫威及其中间体的制备方法 |
| CN114957158A (zh) * | 2022-05-31 | 2022-08-30 | 浙江禾本科技股份有限公司 | 一种制备茚虫威中间体的方法 |
| CN115974808B (zh) * | 2022-12-21 | 2024-03-12 | 大连奇凯医药科技有限公司 | 2-苄基-7-氯[1,2-e]茚并[1,3,4]噁二嗪二甲酸甲酯的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5462938A (en) | 1990-12-21 | 1995-10-31 | Annus; Gary D. | Arthropodicidal oxadiazinyl, thiadiazinyl and triazinyl carboxanilides |
| EP0586551A1 (en) * | 1991-05-24 | 1994-03-16 | E.I. Du Pont De Nemours And Company | Arthropodicidal anilides |
| ES2127270T3 (es) | 1992-03-26 | 1999-04-16 | Du Pont | Amidas artropodicidas. |
| EP0756594B1 (en) | 1994-04-20 | 2002-03-13 | E.I. Du Pont De Nemours And Company | Preparation of arthropodicidal oxadiazines |
-
1997
- 1997-01-31 US US09/230,987 patent/USH1950H1/en not_active Abandoned
- 1997-06-02 IN IN1020CA1997 patent/IN182799B/en unknown
- 1997-06-16 TW TW86108354A patent/TW337984B/zh active
- 1997-06-18 ZA ZA975379A patent/ZA975379B/xx unknown
- 1997-07-31 WO PCT/US1997/013548 patent/WO1998005656A1/en not_active Application Discontinuation
- 1997-07-31 CN CN97196880A patent/CN1226891A/zh active Pending
- 1997-07-31 BR BR9711003A patent/BR9711003A/pt not_active Application Discontinuation
- 1997-07-31 TR TR1999/00224T patent/TR199900224T2/xx unknown
- 1997-07-31 EP EP97936346A patent/EP0922041A1/en not_active Withdrawn
- 1997-07-31 JP JP10508080A patent/JP2001501916A/ja active Pending
- 1997-07-31 AU AU39038/97A patent/AU3903897A/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005323518A (ja) * | 2004-05-13 | 2005-11-24 | Chikuno Shokuhin Kogyo Kk | トコトリエノール含有家禽卵 |
Also Published As
| Publication number | Publication date |
|---|---|
| MX9901054A (en) | 2000-01-01 |
| BR9711003A (pt) | 1999-08-17 |
| WO1998005656A1 (en) | 1998-02-12 |
| ZA975379B (en) | 1998-12-18 |
| EP0922041A1 (en) | 1999-06-16 |
| USH1950H1 (en) | 2001-03-06 |
| TW337984B (en) | 1998-08-11 |
| IN182799B (enrdf_load_stackoverflow) | 1999-07-24 |
| AU3903897A (en) | 1998-02-25 |
| CN1226891A (zh) | 1999-08-25 |
| TR199900224T2 (en) | 1999-04-21 |
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