JPS62192372A - 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 - Google Patents
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Info
- Publication number
- JPS62192372A JPS62192372A JP62022618A JP2261887A JPS62192372A JP S62192372 A JPS62192372 A JP S62192372A JP 62022618 A JP62022618 A JP 62022618A JP 2261887 A JP2261887 A JP 2261887A JP S62192372 A JPS62192372 A JP S62192372A
- Authority
- JP
- Japan
- Prior art keywords
- chlorophenyl
- product
- range
- dimethyl
- hydroxamic acid
- 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
- 238000004519 manufacturing process Methods 0.000 title claims 5
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 title 1
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- BASMANVIUSSIIM-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)benzene Chemical group ClCC1=CC=CC=C1Cl BASMANVIUSSIIM-UHFFFAOYSA-N 0.000 claims description 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 4
- 239000002253 acid Substances 0.000 claims 4
- 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
- QXDOFVVNXBGLKK-UHFFFAOYSA-N 3-Isoxazolidinone Chemical class OC1=NOCC1 QXDOFVVNXBGLKK-UHFFFAOYSA-N 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
- 150000003839 salts Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000002363 herbicidal effect Effects 0.000 description 6
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 5
- 239000004009 herbicide Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 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 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
- 102100023849 Glycophorin-C Human genes 0.000 description 2
- 101100229307 Homo sapiens GYPC gene Proteins 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-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
- UUXRXRHXOZHHJV-UHFFFAOYSA-N 4,4-dimethyl-1,2-oxazolidin-3-one Chemical compound CC1(C)CONC1=O UUXRXRHXOZHHJV-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 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
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 239000000178 monomer Substances 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
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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 true JPS62192372A (ja) | 1987-08-22 |
| JPH0338271B2 JPH0338271B2 (cg-RX-API-DMAC7.html) | 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 (cg-RX-API-DMAC7.html) |
| JP (1) | JPS62192372A (cg-RX-API-DMAC7.html) |
| KR (1) | KR890002426B1 (cg-RX-API-DMAC7.html) |
| BR (1) | BR8700554A (cg-RX-API-DMAC7.html) |
| HU (1) | HU204039B (cg-RX-API-DMAC7.html) |
| IL (1) | IL81542A (cg-RX-API-DMAC7.html) |
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 (cg-RX-API-DMAC7.html) * | 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 HU HU87571A patent/HU204039B/hu unknown
- 1987-02-13 KR KR1019870001193A patent/KR890002426B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| HUT45239A (en) | 1988-06-28 |
| IL81542A (en) | 1991-04-15 |
| BR8700554A (pt) | 1987-12-08 |
| HU204039B (en) | 1991-11-28 |
| IL81542A0 (en) | 1987-09-16 |
| KR870007903A (ko) | 1987-09-22 |
| JPH0338271B2 (cg-RX-API-DMAC7.html) | 1991-06-10 |
| KR890002426B1 (ko) | 1989-07-03 |
| US4742176A (en) | 1988-05-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100558626B1 (ko) | 아실화된 환식 1,3-디카보닐 화합물의 제조 방법 | |
| MXPA06011130A (es) | Proceso para producir un compuesto de 5 - hidroxi - 4 - tiometilpirazol. | |
| KR940009526B1 (ko) | 트리아졸리논의 제조방법 | |
| JPS62192372A (ja) | 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 | |
| Tanaka et al. | Synthesis and reaction of 5‐amino‐3‐trifluoromethylisoxazole and‐pyrazole‐4‐carboxylic acids | |
| JP3140818B2 (ja) | 殺昆虫性、殺線虫性および殺ダニ性の２−ハロ−３−置換−５−アリールピロール化合物の製法 | |
| US5922916A (en) | Process to chloroketoamines using carbamates | |
| US5663365A (en) | Process for the preparation of pyrazolones | |
| CN118359541A (zh) | 砜吡草唑的制备方法 | |
| US7385062B2 (en) | Process for the preparation of phenyltetrazole derivatives | |
| EP0662961A1 (en) | Process of synthesizing useful intermediates of substituted imidazole compounds | |
| SE435278B (sv) | 5-cyano-1-legre(c?711?71-?714)alkyl-pyrrol-2-ettiksyra, framstellning derav och anvendningen som mellanprodukt vid framstellning av terapeutiskt verksamma pyrrolderivat | |
| SU717046A1 (ru) | Способ получени 3-арил-5-фенил-1(4-формилфенил)-2-пиразолинов | |
| WO2004087674A1 (ja) | アクリロニトリル化合物の製造方法 | |
| US4264521A (en) | 5-Halo-4-oxo-2-phenylpentanenitriles | |
| SU553933A3 (ru) | Способ получени 4-амино-1,2,4триазин-5-онов | |
| US6498276B2 (en) | Process for producing acetophenone compound | |
| JP3388046B2 (ja) | チエニルエーテル誘導体の製造方法 | |
| JP2801647B2 (ja) | ６―フルオロクロモン―２―カルボン酸誘導体の製造法 | |
| US6274732B1 (en) | Process for the preparation of 1-[(cyclopent-3-en-1-yl)-methyl]-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione | |
| EP3448837A1 (en) | Process for the preparation of herbicidal pyridinylimidazolone compounds | |
| JP3159860B2 (ja) | ４，５−ジホルミルイミダゾール化合物の合成方法及び新規イミダゾール化合物 | |
| US4281142A (en) | Imidazolecarboxaldehydes | |
| JPS6364429B2 (cg-RX-API-DMAC7.html) | ||
| US5473069A (en) | Preparation of isoxazole-4,5-dicarboxylic diesters |