CN101265224A - 一种制备4-三氟甲硫基苯胺的方法 - Google Patents
一种制备4-三氟甲硫基苯胺的方法 Download PDFInfo
- Publication number
- CN101265224A CN101265224A CNA2008100236964A CN200810023696A CN101265224A CN 101265224 A CN101265224 A CN 101265224A CN A2008100236964 A CNA2008100236964 A CN A2008100236964A CN 200810023696 A CN200810023696 A CN 200810023696A CN 101265224 A CN101265224 A CN 101265224A
- Authority
- CN
- China
- Prior art keywords
- methylthio
- reaction
- mirbane
- trifluoro
- oil
- 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
- OHHHTUXVBNGOGI-UHFFFAOYSA-N 4-(trifluoromethylsulfanyl)aniline Chemical compound NC1=CC=C(SC(F)(F)F)C=C1 OHHHTUXVBNGOGI-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 83
- 239000002994 raw material Substances 0.000 claims abstract description 24
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical class SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 10
- 150000005181 nitrobenzenes Chemical class 0.000 claims abstract description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 54
- 238000002360 preparation method Methods 0.000 claims description 39
- 238000003756 stirring Methods 0.000 claims description 39
- 238000004821 distillation Methods 0.000 claims description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 239000007787 solid Substances 0.000 claims description 26
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 16
- 238000001914 filtration Methods 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 11
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 9
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 claims description 8
- -1 trichloro-methylthio oil of mirbane Chemical compound 0.000 claims description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 7
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 5
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 5
- OLWWBEBYMVVGGY-UHFFFAOYSA-N N,2,3-trifluoro-N-methylsulfanylaniline Chemical compound FC=1C(=C(N(SC)F)C=CC=1)F OLWWBEBYMVVGGY-UHFFFAOYSA-N 0.000 claims description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 4
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 238000013019 agitation Methods 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000012141 concentrate Substances 0.000 claims description 2
- 230000008034 disappearance Effects 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- ODNBVEIAQAZNNM-UHFFFAOYSA-N 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone Chemical compound C1=CC(Cl)=NN2C(C(=O)C)=CN=C21 ODNBVEIAQAZNNM-UHFFFAOYSA-N 0.000 abstract description 4
- GUNJVIDCYZYFGV-UHFFFAOYSA-K Antimony trifluoride Inorganic materials F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 2
- 238000003682 fluorination reaction Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- HDPWHIWTZLBZNQ-UHFFFAOYSA-N oxo-sulfido-[4-(trichloromethyl)phenyl]azanium Chemical compound ClC(C1=CC=C(C=C1)[N+](=S)[O-])(Cl)Cl HDPWHIWTZLBZNQ-UHFFFAOYSA-N 0.000 abstract 2
- KFIMOMYDCZFXKC-UHFFFAOYSA-N (4-methylphenyl)-oxido-sulfanylideneazanium Chemical compound CC1=CC=C([N+]([O-])=S)C=C1 KFIMOMYDCZFXKC-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- CDPMORSLRZTKTG-UHFFFAOYSA-N oxido-sulfanylidene-[4-(trifluoromethyl)phenyl]azanium Chemical compound [O-][N+](=S)C1=CC=C(C(F)(F)F)C=C1 CDPMORSLRZTKTG-UHFFFAOYSA-N 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 description 18
- 238000001035 drying Methods 0.000 description 11
- 238000003760 magnetic stirring Methods 0.000 description 11
- 238000010792 warming Methods 0.000 description 11
- 238000005406 washing Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000273 veterinary drug Substances 0.000 description 9
- ZDFBKZUDCQQKAC-UHFFFAOYSA-N 1-bromo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Br)C=C1 ZDFBKZUDCQQKAC-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 1
- SCCCFNJTCDSLCY-UHFFFAOYSA-N 1-iodo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(I)C=C1 SCCCFNJTCDSLCY-UHFFFAOYSA-N 0.000 description 1
- OCINXEZVIIVXFU-UHFFFAOYSA-N 1-methyl-3-[3-methyl-4-[4-(trifluoromethylthio)phenoxy]phenyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC1=CC(N2C(N(C)C(=O)NC2=O)=O)=CC=C1OC1=CC=C(SC(F)(F)F)C=C1 OCINXEZVIIVXFU-UHFFFAOYSA-N 0.000 description 1
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000001165 anti-coccidial effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 230000000384 rearing effect Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229960000898 toltrazuril Drugs 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (9)
Priority Applications (1)
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CN2008100236964A CN101265224B (zh) | 2008-04-16 | 2008-04-16 | 一种制备4-三氟甲硫基苯胺的方法 |
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CN2008100236964A CN101265224B (zh) | 2008-04-16 | 2008-04-16 | 一种制备4-三氟甲硫基苯胺的方法 |
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CN101265224A true CN101265224A (zh) | 2008-09-17 |
CN101265224B CN101265224B (zh) | 2010-12-08 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104610107A (zh) * | 2015-02-13 | 2015-05-13 | 江苏凌云药业有限公司 | 一种4-三氟甲硫基硝基苯的制备方法 |
CN108947878A (zh) * | 2018-07-24 | 2018-12-07 | 浙江中山化工集团股份有限公司 | 一种2-氯-6-甲硫基甲苯的制备方法 |
CN110483347A (zh) * | 2018-05-14 | 2019-11-22 | 天津师范大学 | 由取代的苯胺制备取代的三氟甲硫基苯的方法 |
CN114773240A (zh) * | 2022-04-23 | 2022-07-22 | 江苏永创医药科技股份有限公司 | 一种利用微通道制备对硝基苯甲硫醚的方法 |
-
2008
- 2008-04-16 CN CN2008100236964A patent/CN101265224B/zh active Active
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104610107A (zh) * | 2015-02-13 | 2015-05-13 | 江苏凌云药业有限公司 | 一种4-三氟甲硫基硝基苯的制备方法 |
CN104610107B (zh) * | 2015-02-13 | 2016-06-15 | 江苏凌云药业有限公司 | 一种4-三氟甲硫基硝基苯的制备方法 |
CN110483347A (zh) * | 2018-05-14 | 2019-11-22 | 天津师范大学 | 由取代的苯胺制备取代的三氟甲硫基苯的方法 |
CN110483347B (zh) * | 2018-05-14 | 2021-03-16 | 天津师范大学 | 由取代的苯胺制备取代的三氟甲硫基苯的方法 |
CN108947878A (zh) * | 2018-07-24 | 2018-12-07 | 浙江中山化工集团股份有限公司 | 一种2-氯-6-甲硫基甲苯的制备方法 |
CN108947878B (zh) * | 2018-07-24 | 2020-07-03 | 浙江中山化工集团股份有限公司 | 一种2-氯-6-甲硫基甲苯的制备方法 |
CN114773240A (zh) * | 2022-04-23 | 2022-07-22 | 江苏永创医药科技股份有限公司 | 一种利用微通道制备对硝基苯甲硫醚的方法 |
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Publication number | Publication date |
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CN101265224B (zh) | 2010-12-08 |
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Owner name: JINTAN LINGYUN ANIMAL HEALTH CO., LTD. Free format text: FORMER OWNER: LINGYUN CHEMICAL FACTORY, JINTAN CITY Effective date: 20110816 |
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Effective date of registration: 20110816 Address after: 213200 Jiangsu city of Jintan Province Jin Cheng Zhen Bai Long Dang Industrial Park B District No. 4 Patentee after: Jintan Lingyun Animal Health Co., Ltd. Address before: 213200 Bailong Industrial Park, Jin Town, Jiangsu, Jintan Patentee before: Lingyun Chemical Factory, Jintan City |
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Effective date of registration: 20170207 Address after: 213200 Jiangsu city in Changzhou Province town of Jintan district on the White Gold Industrial Park B District No. 4 Patentee after: Jiangsu Lingyun pharmaceutical Limited by Share Ltd Address before: 213200 Jiangsu city of Jintan Province Jin Cheng Zhen Bai Long Dang Industrial Park B District No. 4 Patentee before: Jintan Lingyun Animal Health Co., Ltd. |