JPH0481582B2 - - Google Patents
Info
- Publication number
- JPH0481582B2 JPH0481582B2 JP20318884A JP20318884A JPH0481582B2 JP H0481582 B2 JPH0481582 B2 JP H0481582B2 JP 20318884 A JP20318884 A JP 20318884A JP 20318884 A JP20318884 A JP 20318884A JP H0481582 B2 JPH0481582 B2 JP H0481582B2
- Authority
- JP
- Japan
- Prior art keywords
- water
- washed
- chloro
- mixture
- trifluoromethylaniline
- 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
- 150000001875 compounds Chemical class 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- 239000007788 liquid Substances 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 238000004821 distillation Methods 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 7
- -1 2,5-dichloro-3-trifluoromethylaniline 2,5-dichlorobenzotrifluoride Chemical compound 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical class NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- OSTIALFVJOFNPP-UHFFFAOYSA-N 1-bromo-4-chloro-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Cl)=CC=C1Br OSTIALFVJOFNPP-UHFFFAOYSA-N 0.000 description 2
- NDZJSUCUYPZXPR-UHFFFAOYSA-N 1-nitro-2-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=CC=C1C(F)(F)F NDZJSUCUYPZXPR-UHFFFAOYSA-N 0.000 description 2
- HOXARLOFJWVUQH-UHFFFAOYSA-N 2,5-dichloro-1-nitro-3-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1Cl HOXARLOFJWVUQH-UHFFFAOYSA-N 0.000 description 2
- JPQADMWPLDPPKO-UHFFFAOYSA-N 2-chloro-5-fluoro-3-(trifluoromethyl)aniline Chemical compound NC1=CC(F)=CC(C(F)(F)F)=C1Cl JPQADMWPLDPPKO-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- IRZPMVXKUOUERU-UHFFFAOYSA-N 5-bromo-2-chloro-1-nitro-3-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Br)=CC(C(F)(F)F)=C1Cl IRZPMVXKUOUERU-UHFFFAOYSA-N 0.000 description 2
- JJHIPAVNYPOJRL-UHFFFAOYSA-N 5-bromo-2-chloro-3-(trifluoromethyl)aniline Chemical compound NC1=CC(Br)=CC(C(F)(F)F)=C1Cl JJHIPAVNYPOJRL-UHFFFAOYSA-N 0.000 description 2
- YIIDCLDBMNVOAQ-UHFFFAOYSA-N 5-chloro-2-fluoro-1-nitro-3-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1F YIIDCLDBMNVOAQ-UHFFFAOYSA-N 0.000 description 2
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 2
- 241000256248 Spodoptera Species 0.000 description 2
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- DGRVQOKCSKDWIH-UHFFFAOYSA-N 1-chloro-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1Cl DGRVQOKCSKDWIH-UHFFFAOYSA-N 0.000 description 1
- CBMMVERXHJUMCM-UHFFFAOYSA-N 1-chloro-4-fluoro-2-(trifluoromethyl)benzene Chemical compound FC1=CC=C(Cl)C(C(F)(F)F)=C1 CBMMVERXHJUMCM-UHFFFAOYSA-N 0.000 description 1
- GBOWGKOVMBDPJF-UHFFFAOYSA-N 1-fluoro-3-(trifluoromethyl)benzene Chemical compound FC1=CC=CC(C(F)(F)F)=C1 GBOWGKOVMBDPJF-UHFFFAOYSA-N 0.000 description 1
- IFDZNBVEINMRLU-UHFFFAOYSA-N 1-phenyl-1-(trifluoromethyl)urea Chemical class NC(=O)N(C(F)(F)F)C1=CC=CC=C1 IFDZNBVEINMRLU-UHFFFAOYSA-N 0.000 description 1
- DUWMUFIUYCJZSF-UHFFFAOYSA-N 2,5-difluoro-3-(trifluoromethyl)aniline Chemical compound NC1=CC(F)=CC(C(F)(F)F)=C1F DUWMUFIUYCJZSF-UHFFFAOYSA-N 0.000 description 1
- XGOCKBMEZPNDPJ-UHFFFAOYSA-N 4-bromo-1-chloro-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Br)=CC=C1Cl XGOCKBMEZPNDPJ-UHFFFAOYSA-N 0.000 description 1
- ASPDJZINBYYZRU-UHFFFAOYSA-N 5-amino-2-chlorobenzotrifluoride Chemical compound NC1=CC=C(Cl)C(C(F)(F)F)=C1 ASPDJZINBYYZRU-UHFFFAOYSA-N 0.000 description 1
- DCLOBGIFIKDYRR-UHFFFAOYSA-N 5-chloro-2-fluoro-3-(trifluoromethyl)aniline Chemical compound NC1=CC(Cl)=CC(C(F)(F)F)=C1F DCLOBGIFIKDYRR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 244000017020 Ipomoea batatas Species 0.000 description 1
- 235000002678 Ipomoea batatas Nutrition 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZWYSLPOHOBPSLC-UHFFFAOYSA-N n-benzoyl-n'-phenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC(=O)C1=CC=CC=C1 ZWYSLPOHOBPSLC-UHFFFAOYSA-N 0.000 description 1
- MPNZRDLYXIEUSQ-UHFFFAOYSA-N n-chloro-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC=CC(NCl)=C1 MPNZRDLYXIEUSQ-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000005181 nitrobenzenes Chemical class 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20318884A JPS6183146A (ja) | 1984-09-28 | 1984-09-28 | ２，５−ジハロ−３−トリフルオロメチルアニリン及びその製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20318884A JPS6183146A (ja) | 1984-09-28 | 1984-09-28 | ２，５−ジハロ−３−トリフルオロメチルアニリン及びその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6183146A JPS6183146A (ja) | 1986-04-26 |
| JPH0481582B2 true JPH0481582B2 (fr) | 1992-12-24 |
Family
ID=16469915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20318884A Granted JPS6183146A (ja) | 1984-09-28 | 1984-09-28 | ２，５−ジハロ−３−トリフルオロメチルアニリン及びその製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6183146A (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5149810A (en) * | 1988-04-22 | 1992-09-22 | Imperial Chemical Industries Plc | Pyrimidine compounds |
| GB8906946D0 (en) * | 1988-04-22 | 1989-05-10 | Ici Plc | Novel compounds |
| GB8908638D0 (en) * | 1989-04-17 | 1989-06-01 | Ici Plc | Novel compounds |
| CN114920655A (zh) * | 2022-07-07 | 2022-08-19 | 南京正荣医药化学有限公司 | 一种2-氟-3-三氟甲基苯胺的制备方法 |
-
1984
- 1984-09-28 JP JP20318884A patent/JPS6183146A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6183146A (ja) | 1986-04-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH06199763A (ja) | 殺虫性ｎ′−置換−ｎ，ｎ′−ジアシルヒドラジン | |
| JPH0481582B2 (fr) | ||
| EP0119892B1 (fr) | Nouveau dérivés de l'hydroxylamine, leur procédé de préparation, leur application comme facteur de croissance des végétaux et les compositions les renfermant | |
| JP2771994B2 (ja) | プロペン酸誘導体の製造法 | |
| US4730062A (en) | Process of preparation of tetrafluoro 2,3-dihydrobenzofurans | |
| EP0031218B1 (fr) | Composé 2-amino-trifluorométhyl-halogénopyridine et procédé pour sa préparation | |
| FR2495609A1 (fr) | Acylurees, procedes pour les preparer et produits insecticides contenant de tels composes | |
| US5672765A (en) | Process for the preparation of aromatic fluorinated compounds and novel diamides | |
| US5484953A (en) | O-phenylenediamines containing fluoroalkyl(ene) groups | |
| KR950013107B1 (ko) | 제초성 디페닐 에테르 유도체의 제조방법 | |
| JP3438084B2 (ja) | ３，４−ジクロロベンゾニトリルの製造法 | |
| JPH01149755A (ja) | 芳香族核中に弗素を含有しているフルオロメトキシ‐アミノベンゼン類およびフルオロメチルチオ‐アミノベンゼン類並びにそれらの製造方法 | |
| JP3640319B2 (ja) | ベンズアミド誘導体の製造方法 | |
| JPS62298562A (ja) | ブロモアニリン類の製造法 | |
| DE2062349A1 (de) | Aminoaryloxy-ary!carbonsäurenitrile und ein Verfahren zu ihrer Herstellung | |
| JPH0830065B2 (ja) | フルオル化された▲下０▼−ジアミノベンゾ−１，４−ジオキセン類の製造法 | |
| JP2951002B2 (ja) | ４−置換５−クロル−２−ヒドラジノチアゾール及びその製造用の中間体 | |
| JP2686947B2 (ja) | ２−（フェニルウレイド）アミノフェノール類の製造方法 | |
| JPS6350339B2 (fr) | ||
| JP4390964B2 (ja) | 新規ハロゲン化剤 | |
| JPH10265449A (ja) | 置換ベンゾニトリルの製造方法 | |
| EP0596130B1 (fr) | Production de 2-halo-3,5-difluoroaniline, intermediaire servant a produire ce compose, et production dudit intermediaire | |
| CH652384A5 (fr) | Procede de preparation d'acides phenoxybenzoiques. | |
| BE901066A (fr) | Composes chimiues intermediiares pour la preparation d'aniline substituee et procede de preparation. | |
| JPS62185064A (ja) | Ｎ−ベンゾイル−ｎ′−フエノキシフエニル尿素及びその製法 |