JPWO2019208643A5 - - Google Patents
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- Publication number
- JPWO2019208643A5 JPWO2019208643A5 JP2020515529A JP2020515529A JPWO2019208643A5 JP WO2019208643 A5 JPWO2019208643 A5 JP WO2019208643A5 JP 2020515529 A JP2020515529 A JP 2020515529A JP 2020515529 A JP2020515529 A JP 2020515529A JP WO2019208643 A5 JPWO2019208643 A5 JP WO2019208643A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- hydroxylamine
- formula
- compound
- reaction
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims 18
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 10
- 239000002253 acid Substances 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 8
- 239000003054 catalyst Substances 0.000 claims 7
- 150000007513 acids Chemical class 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 5
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims 4
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000003377 acid catalyst Substances 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 230000003472 neutralizing effect Effects 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims 2
- ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- 229940117389 dichlorobenzene Drugs 0.000 claims 2
- 150000002443 hydroxylamines Chemical class 0.000 claims 2
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 claims 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 2
- 239000011976 maleic acid Substances 0.000 claims 2
- 239000011707 mineral Substances 0.000 claims 2
- 235000010755 mineral Nutrition 0.000 claims 2
- 229910017604 nitric acid Inorganic materials 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 150000003460 sulfonic acids Chemical class 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- SEPQTYODOKLVSB-UHFFFAOYSA-N 3-methylbut-2-enal Chemical compound CC(C)=CC=O SEPQTYODOKLVSB-UHFFFAOYSA-N 0.000 claims 1
- DIYSFZUJSGOINT-UHFFFAOYSA-N 5,5-dimethyl-4h-1,2-oxazole Chemical compound CC1(C)CC=NO1 DIYSFZUJSGOINT-UHFFFAOYSA-N 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical compound O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000011736 potassium bicarbonate Substances 0.000 claims 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims 1
- 235000015497 potassium bicarbonate Nutrition 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 235000011181 potassium carbonates Nutrition 0.000 claims 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims 1
- 235000011118 potassium hydroxide Nutrition 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 235000017550 sodium carbonate Nutrition 0.000 claims 1
- 235000011121 sodium hydroxide Nutrition 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2018086679 | 2018-04-27 | ||
| JP2018086679 | 2018-04-27 | ||
| PCT/JP2019/017459 WO2019208643A1 (ja) | 2018-04-27 | 2019-04-24 | ５，５－ジ置換－４，５－ジヒドロイソオキサゾールの製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPWO2019208643A1 JPWO2019208643A1 (ja) | 2021-05-13 |
| JPWO2019208643A5 true JPWO2019208643A5 (enExample) | 2022-12-06 |
| JP7242641B2 JP7242641B2 (ja) | 2023-03-20 |
Family
ID=68295226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020515529A Active JP7242641B2 (ja) | 2018-04-27 | 2019-04-24 | ５，５－ジ置換－４，５－ジヒドロイソオキサゾールの製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US11753384B2 (enExample) |
| EP (1) | EP3789382B1 (enExample) |
| JP (1) | JP7242641B2 (enExample) |
| CN (1) | CN112004805B (enExample) |
| IL (1) | IL278229B2 (enExample) |
| MX (1) | MX2020011267A (enExample) |
| TW (1) | TWI810284B (enExample) |
| WO (1) | WO2019208643A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111491926B (zh) * | 2017-12-15 | 2022-07-15 | 组合化学工业株式会社 | 5,5-二取代-4,5-二氢异噁唑的新型制造方法 |
| CN113891882B (zh) | 2019-06-14 | 2024-11-26 | 组合化学工业株式会社 | 二氢异噁唑的制造方法 |
| CN114644602B (zh) * | 2020-12-17 | 2024-09-03 | 帕潘纳(北京)科技有限公司 | 二氢异噁唑类化合物的制备方法 |
| CN115073390B (zh) * | 2021-03-11 | 2024-08-06 | 山东润博生物科技有限公司 | 一种4,5-二氢异噁唑衍生物及其制备方法和应用 |
| CN116178294A (zh) * | 2023-01-08 | 2023-05-30 | 湖南吴赣药业有限公司 | 一种制备5,5-二甲基-4,5-二氢异噁唑的方法 |
| CN117285479B (zh) * | 2023-09-26 | 2024-07-23 | 山东滨农科技有限公司 | 一种3-氯-5,5-二甲基-4,5-二氢异噁唑的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU3329800A (en) | 1999-03-29 | 2000-10-16 | Nippon Soda Co., Ltd. | Process for the preparation of (e)-3-(1-propenyl)isoxazoline |
| JP4465133B2 (ja) | 2001-02-08 | 2010-05-19 | クミアイ化学工業株式会社 | イソオキサゾリン誘導体及びこれを有効成分とする除草剤 |
| TWI649303B (zh) | 2007-08-17 | 2019-02-01 | 杜邦股份有限公司 | 製備４-乙醯基-ｎ-〔２-側氧基-２-〔（２，２，２-三氟乙基）胺基〕乙基〕-１-萘甲醯胺之化合物及方法 |
| ES2467969T3 (es) | 2009-11-26 | 2014-06-13 | Basf Se | Procedimiento para la preparación de 2-isoxazolinas 5,5-disustituidas |
| WO2012056478A1 (en) | 2010-10-30 | 2012-05-03 | Lupin Limited | Oxazole and isoxazole crac modulators |
| CN107652245B (zh) * | 2017-08-24 | 2019-09-13 | 郑州手性药物研究院有限公司 | 手性双苯噁唑酸乙酯化合物及其制备方法和应用 |
| CN111491926B (zh) | 2017-12-15 | 2022-07-15 | 组合化学工业株式会社 | 5,5-二取代-4,5-二氢异噁唑的新型制造方法 |
-
2019
- 2019-04-24 EP EP19793641.2A patent/EP3789382B1/en active Active
- 2019-04-24 CN CN201980025644.7A patent/CN112004805B/zh active Active
- 2019-04-24 IL IL278229A patent/IL278229B2/en unknown
- 2019-04-24 MX MX2020011267A patent/MX2020011267A/es unknown
- 2019-04-24 TW TW108114335A patent/TWI810284B/zh active
- 2019-04-24 WO PCT/JP2019/017459 patent/WO2019208643A1/ja not_active Ceased
- 2019-04-24 JP JP2020515529A patent/JP7242641B2/ja active Active
- 2019-04-24 US US17/049,128 patent/US11753384B2/en active Active
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