JPH0338271B2 - - Google Patents
Info
- Publication number
- JPH0338271B2 JPH0338271B2 JP62022618A JP2261887A JPH0338271B2 JP H0338271 B2 JPH0338271 B2 JP H0338271B2 JP 62022618 A JP62022618 A JP 62022618A JP 2261887 A JP2261887 A JP 2261887A JP H0338271 B2 JPH0338271 B2 JP H0338271B2
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- range
- product
- isoxazolidinone
- manufacturing
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 claims description 14
- QXDOFVVNXBGLKK-UHFFFAOYSA-N 3-Isoxazolidinone Chemical class OC1=NOCC1 QXDOFVVNXBGLKK-UHFFFAOYSA-N 0.000 claims description 5
- BASMANVIUSSIIM-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)benzene Chemical group ClCC1=CC=CC=C1Cl BASMANVIUSSIIM-UHFFFAOYSA-N 0.000 claims description 4
- LOBXXWMXAMOBAH-UHFFFAOYSA-N 3-chloro-n-hydroxy-2,2-dimethylpropanamide Chemical compound ClCC(C)(C)C(=O)NO LOBXXWMXAMOBAH-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims 5
- TWPQMKAIJRMOGL-UHFFFAOYSA-N 3-chloro-n-hydroxypropanamide Chemical class ONC(=O)CCCl TWPQMKAIJRMOGL-UHFFFAOYSA-N 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- -1 benzyl halide Chemical class 0.000 claims 2
- 150000004679 hydroxides Chemical class 0.000 claims 2
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000002363 herbicidal effect Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- ZNTBTPJHUYEBPT-UHFFFAOYSA-N 1-[(2-chlorophenyl)methoxy]-3,3-dimethylazetidin-2-one Chemical compound O=C1C(C)(C)CN1OCC1=CC=CC=C1Cl ZNTBTPJHUYEBPT-UHFFFAOYSA-N 0.000 description 3
- UUXRXRHXOZHHJV-UHFFFAOYSA-N 4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound CC1(C)CONC1=O UUXRXRHXOZHHJV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- DGMHDMJURFIFKT-UHFFFAOYSA-N 3-[(2-chlorophenyl)methoxy]-4,4-dimethyl-5h-1,2-oxazole Chemical compound CC1(C)CON=C1OCC1=CC=CC=C1Cl DGMHDMJURFIFKT-UHFFFAOYSA-N 0.000 description 2
- MQZNDDUMJVSIMH-UHFFFAOYSA-N 3-chloro-2,2-dimethylpropanoyl chloride Chemical compound ClCC(C)(C)C(Cl)=O MQZNDDUMJVSIMH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- ATDOYFPHCIRHKH-UHFFFAOYSA-N n-hydroxy-2,2-dimethylpropanamide Chemical class CC(C)(C)C(=O)NO ATDOYFPHCIRHKH-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- PCJBPVQBPIEIRV-UHFFFAOYSA-N 2-[(2-chlorophenyl)methoxy]-4,4-dimethyl-1,2-oxazolidine Chemical compound C1C(C)(C)CON1OCC1=CC=CC=C1Cl PCJBPVQBPIEIRV-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- DIOLYBIMJOQMOO-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanamide Chemical compound OCC(C)(C)C(N)=O DIOLYBIMJOQMOO-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
- 239000012066 reaction slurry Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/829,337 US4742176A (en) | 1986-02-14 | 1986-02-14 | Process for 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone |
| US829337 | 1986-02-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62192372A JPS62192372A (ja) | 1987-08-22 |
| JPH0338271B2 true JPH0338271B2 (OSRAM) | 1991-06-10 |
Family
ID=25254241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62022618A Granted JPS62192372A (ja) | 1986-02-14 | 1987-02-04 | ２−〔（２−クロロフエニル）メチル〕−４，４−ジメチル−３−イソオキサゾリジノンの製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4742176A (OSRAM) |
| JP (1) | JPS62192372A (OSRAM) |
| KR (1) | KR890002426B1 (OSRAM) |
| BR (1) | BR8700554A (OSRAM) |
| HU (1) | HU204039B (OSRAM) |
| IL (1) | IL81542A (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5055328A (en) * | 1989-06-16 | 1991-10-08 | Viskase Corporation | Differentially cross-linked multilayer film |
| US5066665A (en) * | 1990-05-21 | 1991-11-19 | Warner-Lambert Co. | Substituted isoxazolidin-3-ones and derivatives thereof acting at muscarinic receptors |
| GB2515783B (en) * | 2013-07-03 | 2018-07-11 | Rotam Agrochem Int Co Ltd | Process for preparing clomazone, a form and use of the same |
| CN106749072A (zh) * | 2016-11-12 | 2017-05-31 | 江苏长青生物科技有限公司 | 异恶草酮的制备方法 |
| CN108774186B (zh) * | 2018-07-30 | 2022-03-11 | 潍坊先达化工有限公司 | 一种双极膜电渗析法制备异噁草松的方法 |
| CN110172042A (zh) * | 2019-05-15 | 2019-08-27 | 江苏禾本生化有限公司 | 一种异噁草酮的低温合成工艺 |
| CN113620896A (zh) * | 2021-08-31 | 2021-11-09 | 青岛科技大学 | 2-(2-氯苯基)甲基-4,4-二甲基-3-异恶唑酮的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2862001A (en) * | 1955-07-22 | 1958-11-25 | Hoffmann La Roche | Process for the manufacture of an isoxazolidone compound |
| NL6402375A (OSRAM) * | 1964-03-07 | 1965-09-08 | ||
| US3364110A (en) * | 1964-08-10 | 1968-01-16 | Hoffmann La Roche | Method for preventing coccidiosis with certain benzohydroxamic acid derivatives |
| US3475485A (en) * | 1967-02-08 | 1969-10-28 | American Home Prod | Dibenzocycloheptene-5-hydroxamic acid and ether and carbonyl derivatives thereof |
| US4455430A (en) * | 1979-07-31 | 1984-06-19 | The Upjohn Company | Process for preparing tricholomic acid and derivatives thereof |
| US4405357A (en) * | 1980-06-02 | 1983-09-20 | Fmc Corporation | Herbicidal 3-isoxazolidinones and hydroxamic acids |
| US4337197A (en) * | 1980-10-31 | 1982-06-29 | E. R. Squibb & Sons, Inc. | O-sulfated β-lactam hydroxamic acids and intermediates |
-
1986
- 1986-02-14 US US06/829,337 patent/US4742176A/en not_active Expired - Lifetime
-
1987
- 1987-02-04 JP JP62022618A patent/JPS62192372A/ja active Granted
- 1987-02-06 BR BR8700554A patent/BR8700554A/pt not_active IP Right Cessation
- 1987-02-11 IL IL81542A patent/IL81542A/xx not_active IP Right Cessation
- 1987-02-13 KR KR1019870001193A patent/KR890002426B1/ko not_active Expired
- 1987-02-13 HU HU87571A patent/HU204039B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR890002426B1 (ko) | 1989-07-03 |
| IL81542A (en) | 1991-04-15 |
| KR870007903A (ko) | 1987-09-22 |
| IL81542A0 (en) | 1987-09-16 |
| US4742176A (en) | 1988-05-03 |
| JPS62192372A (ja) | 1987-08-22 |
| HU204039B (en) | 1991-11-28 |
| BR8700554A (pt) | 1987-12-08 |
| HUT45239A (en) | 1988-06-28 |
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