JP2002519409A - ２−ニトロ−５−（フェニルチオ）−アニリンの製造方法 - Google Patents
２−ニトロ−５−（フェニルチオ）−アニリンの製造方法Info
- Publication number
- JP2002519409A JP2002519409A JP2000558074A JP2000558074A JP2002519409A JP 2002519409 A JP2002519409 A JP 2002519409A JP 2000558074 A JP2000558074 A JP 2000558074A JP 2000558074 A JP2000558074 A JP 2000558074A JP 2002519409 A JP2002519409 A JP 2002519409A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- nitroaniline
- chloro
- reaction
- represented
- 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.)
- Withdrawn
Links
- AJGJUXSVUPXOHL-UHFFFAOYSA-N 2-nitro-5-phenylsulfanylaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC(SC=2C=CC=CC=2)=C1 AJGJUXSVUPXOHL-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims abstract description 70
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 52
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 25
- ZCWXYZBQDNFULS-UHFFFAOYSA-N 5-chloro-2-nitroaniline Chemical compound NC1=CC(Cl)=CC=C1[N+]([O-])=O ZCWXYZBQDNFULS-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 239000000010 aprotic solvent Substances 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 claims description 3
- QUIMTLZDMCNYGY-UHFFFAOYSA-N 2,4-dichloro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1Cl QUIMTLZDMCNYGY-UHFFFAOYSA-N 0.000 claims description 2
- JMYWFKZHEPVSIS-UHFFFAOYSA-N 3-phenylsulfanylaniline Chemical compound NC1=CC=CC(SC=2C=CC=CC=2)=C1 JMYWFKZHEPVSIS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 230000002269 spontaneous effect Effects 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- AWZRAQWGIUYTOH-UHFFFAOYSA-N n-chloro-2-nitroaniline Chemical compound [O-][N+](=O)C1=CC=CC=C1NCl AWZRAQWGIUYTOH-UHFFFAOYSA-N 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 8
- 239000003444 phase transfer catalyst Substances 0.000 description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000002798 polar solvent Substances 0.000 description 5
- 239000002351 wastewater Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- -1 for example Chemical compound 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- CMVQZRLQEOAYSW-UHFFFAOYSA-N 1,2-dichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1Cl CMVQZRLQEOAYSW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 102100024522 Bladder cancer-associated protein Human genes 0.000 description 1
- 101150110835 Blcap gene Proteins 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 101100493740 Oryza sativa subsp. japonica BC10 gene Proteins 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical group 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000007938 chlorocyclic compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000007952 growth promoter Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19829357.7 | 1998-07-01 | ||
| DE19829357A DE19829357A1 (de) | 1998-07-01 | 1998-07-01 | Verfahren zur Herstellung von 2-Nitro-5-(phenylthio)-anilinen |
| PCT/EP1999/004296 WO2000001669A2 (de) | 1998-07-01 | 1999-06-21 | Verfahren zur herstellung von 2-nitro-5-(phenylthio)-anilinen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002519409A true JP2002519409A (ja) | 2002-07-02 |
| JP2002519409A5 JP2002519409A5 (enExample) | 2006-04-06 |
Family
ID=7872608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000558074A Withdrawn JP2002519409A (ja) | 1998-07-01 | 1999-06-21 | ２−ニトロ−５−（フェニルチオ）−アニリンの製造方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6552230B1 (enExample) |
| EP (1) | EP1091935B1 (enExample) |
| JP (1) | JP2002519409A (enExample) |
| CN (1) | CN1178908C (enExample) |
| AT (1) | ATE264838T1 (enExample) |
| AU (1) | AU4614399A (enExample) |
| BR (1) | BR9911763A (enExample) |
| DE (2) | DE19829357A1 (enExample) |
| HU (1) | HUP0102237A3 (enExample) |
| IL (1) | IL139947A0 (enExample) |
| WO (1) | WO2000001669A2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7030109B2 (en) | 1999-07-19 | 2006-04-18 | Pharmacia & Upjohn Company | 1,2,3,4,5,6-Hexahydroazepino[4,5-b]indoles containing arylsulfones at the 9-position |
| MY122278A (en) * | 1999-07-19 | 2006-04-29 | Upjohn Co | 1,2,3,4,5,6-hexahydroazepino[4,5-b]indoles containing arylsulfones at the 9-position |
| CN102351715A (zh) * | 2011-09-05 | 2012-02-15 | 江苏隆昌化工有限公司 | 高纯度邻硝基对氯苯胺的生产工艺 |
| CN102603584B (zh) * | 2012-02-23 | 2014-04-16 | 江西仁明医药化工有限公司 | 2-氨基二苯硫醚的制备方法 |
| CN103242238B (zh) * | 2013-05-10 | 2016-04-20 | 常州齐晖药业有限公司 | 一种芬苯达唑的制备方法 |
| CN108299259B (zh) * | 2018-01-16 | 2020-08-07 | 珠海优润医药科技有限公司 | 2-氨基-5-苯硫基-(2-甲氧基)乙酰苯胺的制备方法 |
| CN111499549B (zh) * | 2020-04-20 | 2022-04-22 | 山东国邦药业有限公司 | 一种制备芬苯达唑中间体2-硝基-4-苯硫基苯胺的方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1028337A (en) | 1973-02-12 | 1978-03-21 | Syntex (U.S.A.) Llc | Carbalkoxythioureidobenzene derivatives having anthelmintic properties |
| DE2332398A1 (de) | 1973-06-26 | 1975-01-23 | Hoechst Ag | 2-carbalkoxy-amino-benzimidazol-5(6)phenylaether, ihre herstellung und verwendung in mitteln gegen helminthen |
| GB1479624A (en) | 1974-11-05 | 1977-07-13 | May & Baker Ltd | (3-alkoxycarbonyl-2-thioureido)benzene derivatives |
| US4011320A (en) | 1975-06-23 | 1977-03-08 | Syntex (U.S.A.) Inc. | 7(8)-substituted triazinobenzimidazoles and anthelmintic compositions and method |
| CH619458A5 (en) | 1976-01-14 | 1980-09-30 | Ciba Geigy Ag | Process for the preparation of a quinoxaline derivative |
| DE3110894A1 (de) | 1981-03-20 | 1982-09-30 | Celamerck Gmbh & Co Kg, 6507 Ingelheim | Neue nitroaniline |
| DE3431827A1 (de) | 1984-08-30 | 1986-03-13 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von chlor-o-nitroanilinen |
| PL288866A1 (en) | 1991-01-25 | 1992-07-27 | Politechnika Slaska Im Wincent | Method of obtaining 2-nitro-5-phenylthioanilin |
-
1998
- 1998-07-01 DE DE19829357A patent/DE19829357A1/de not_active Withdrawn
-
1999
- 1999-06-21 BR BR9911763-0A patent/BR9911763A/pt not_active IP Right Cessation
- 1999-06-21 HU HU0102237A patent/HUP0102237A3/hu unknown
- 1999-06-21 WO PCT/EP1999/004296 patent/WO2000001669A2/de not_active Ceased
- 1999-06-21 AU AU46143/99A patent/AU4614399A/en not_active Abandoned
- 1999-06-21 JP JP2000558074A patent/JP2002519409A/ja not_active Withdrawn
- 1999-06-21 CN CNB998082104A patent/CN1178908C/zh not_active Expired - Fee Related
- 1999-06-21 EP EP99929294A patent/EP1091935B1/de not_active Expired - Lifetime
- 1999-06-21 AT AT99929294T patent/ATE264838T1/de not_active IP Right Cessation
- 1999-06-21 IL IL13994799A patent/IL139947A0/xx unknown
- 1999-06-21 DE DE59909246T patent/DE59909246D1/de not_active Expired - Fee Related
- 1999-06-21 US US09/720,011 patent/US6552230B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1308607A (zh) | 2001-08-15 |
| HUP0102237A2 (hu) | 2001-10-28 |
| DE59909246D1 (de) | 2004-05-27 |
| WO2000001669A3 (de) | 2000-02-10 |
| EP1091935A2 (de) | 2001-04-18 |
| EP1091935B1 (de) | 2004-04-21 |
| WO2000001669A2 (de) | 2000-01-13 |
| IL139947A0 (en) | 2002-02-10 |
| BR9911763A (pt) | 2001-04-03 |
| AU4614399A (en) | 2000-01-24 |
| ATE264838T1 (de) | 2004-05-15 |
| US6552230B1 (en) | 2003-04-22 |
| HUP0102237A3 (en) | 2002-12-28 |
| DE19829357A1 (de) | 2000-01-05 |
| CN1178908C (zh) | 2004-12-08 |
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Legal Events
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| A521 | Request for written amendment filed |
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| A621 | Written request for application examination |
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| A761 | Written withdrawal of application |
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