DD144771A5 - Verfahren zur herstellung von acetaniliden - Google Patents

Verfahren zur herstellung von acetaniliden Download PDF

Info

Publication number: DD144771A5
Authority: DD; German Democratic Republic
Prior art keywords: carbon atoms; parts; weight; chloro; alkyl
Prior art date: 1978-07-13

Application number

DD79214273A

Other languages

German (de)

English (en)

Inventor

Karl Eicken

Wolfgang Rohr

Friedrich Linhart

Original Assignee

Basf Ag

Priority date (The priority date 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 date listed.)

1978-07-13

Filing date

1979-07-11

Publication date

1980-11-05

1979-07-11 Application filed by Basf Ag filed Critical Basf Ag

1980-11-05 Publication of DD144771A5 publication Critical patent/DD144771A5/de

Links

150000008061 acetanilides Chemical class 0.000 title description 7
238000000034 method Methods 0.000 title description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 9
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical group 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
-1 phenyl radicals Chemical class 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 3
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Chemical group 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
239000012071 phase Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
239000003444 phase transfer catalyst Substances 0.000 description 7
UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 5
239000007858 starting material Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
229960001413 acetanilide Drugs 0.000 description 4
238000002156 mixing Methods 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
VRWJZGHUCOFGPZ-UHFFFAOYSA-N 2-{[4-(4-pyridin-4-yl-1h-pyrazol-3-yl)phenoxy]methyl}quinoline Chemical compound C=1C=C2C=CC=CC2=NC=1COC(C=C1)=CC=C1C1=NNC=C1C1=CC=NC=C1 VRWJZGHUCOFGPZ-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
239000003513 alkali Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
150000002431 hydrogen Chemical group 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
BDXJANJAHYKTMI-UHFFFAOYSA-N 2,3,4,5-tetramethyl-1h-pyrrole Chemical compound CC=1NC(C)=C(C)C=1C BDXJANJAHYKTMI-UHFFFAOYSA-N 0.000 description 2
NCFMDIJKEYGCRD-UHFFFAOYSA-N 4-methoxy-1h-pyrazole Chemical compound COC=1C=NNC=1 NCFMDIJKEYGCRD-UHFFFAOYSA-N 0.000 description 2
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
150000003851 azoles Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000007717 exclusion Effects 0.000 description 2
RIKMMFOAQPJVMX-UHFFFAOYSA-N fomepizole Chemical compound CC=1C=NNC=1 RIKMMFOAQPJVMX-UHFFFAOYSA-N 0.000 description 2
229960004285 fomepizole Drugs 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
150000004010 onium ions Chemical class 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000000926 separation method Methods 0.000 description 2
235000002639 sodium chloride Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
150000000177 1,2,3-triazoles Chemical class 0.000 description 1
150000000178 1,2,4-triazoles Chemical class 0.000 description 1
VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 1
JCGGPCDDFXIVQB-UHFFFAOYSA-N 2,4,5-tribromo-1h-imidazole Chemical compound BrC1=NC(Br)=C(Br)N1 JCGGPCDDFXIVQB-UHFFFAOYSA-N 0.000 description 1
VMLODBFMRBFTTR-UHFFFAOYSA-N 2-chloro-n-(2,6-dimethylphenyl)-n-[(4-propan-2-ylpyrazol-1-yl)methyl]acetamide Chemical compound C1=C(C(C)C)C=NN1CN(C(=O)CCl)C1=C(C)C=CC=C1C VMLODBFMRBFTTR-UHFFFAOYSA-N 0.000 description 1
OCVXSFKKWXMYPF-UHFFFAOYSA-N 2-chloroimidazole Chemical compound ClC1=NC=CN1 OCVXSFKKWXMYPF-UHFFFAOYSA-N 0.000 description 1
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
HUVAAOZUPLEYBH-UHFFFAOYSA-N 3,4,5-trimethyl-1h-pyrazole Chemical compound CC1=NNC(C)=C1C HUVAAOZUPLEYBH-UHFFFAOYSA-N 0.000 description 1
NGDDUAYSWPUSLX-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)-1h-pyrazole Chemical compound FC(F)(F)C=1C=C(C(F)(F)F)NN=1 NGDDUAYSWPUSLX-UHFFFAOYSA-N 0.000 description 1
FRAKFBWDPXYIQO-UHFFFAOYSA-N 3,5-dibromo-1h-1,2,4-triazole Chemical compound BrC1=NNC(Br)=N1 FRAKFBWDPXYIQO-UHFFFAOYSA-N 0.000 description 1
JNTFFNKMQMJJQZ-UHFFFAOYSA-N 3,5-dichloro-1h-1,2,4-triazole Chemical compound ClC1=NNC(Cl)=N1 JNTFFNKMQMJJQZ-UHFFFAOYSA-N 0.000 description 1
SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
XYCFDUUGHDYLAL-UHFFFAOYSA-N 3-[[3-(2-carboxyethoxy)-4-methyl-1H-pyrazol-5-yl]oxy]propanoic acid Chemical compound CC=1C(=NNC=1OCCC(=O)O)OCCC(=O)O XYCFDUUGHDYLAL-UHFFFAOYSA-N 0.000 description 1
MYYYOBVDIRECDX-UHFFFAOYSA-N 4,5-dibromo-1h-imidazole Chemical compound BrC=1N=CNC=1Br MYYYOBVDIRECDX-UHFFFAOYSA-N 0.000 description 1
QAJJXHRQPLATMK-UHFFFAOYSA-N 4,5-dichloro-1h-imidazole Chemical compound ClC=1N=CNC=1Cl QAJJXHRQPLATMK-UHFFFAOYSA-N 0.000 description 1
QCJPFRGDWAGMDB-UHFFFAOYSA-N 4,5-dichloro-2-ethyl-1h-imidazole Chemical compound CCC1=NC(Cl)=C(Cl)N1 QCJPFRGDWAGMDB-UHFFFAOYSA-N 0.000 description 1
WVGCPEDBFHEHEZ-UHFFFAOYSA-N 4-bromo-1h-pyrazole Chemical compound BrC=1C=NNC=1 WVGCPEDBFHEHEZ-UHFFFAOYSA-N 0.000 description 1
RISOHYOEPYWKOB-UHFFFAOYSA-N 4-bromo-3,5-dimethyl-1h-pyrazole Chemical compound CC1=NNC(C)=C1Br RISOHYOEPYWKOB-UHFFFAOYSA-N 0.000 description 1
BADSZRMNXWLUKO-UHFFFAOYSA-N 4-chloro-1h-pyrazole Chemical compound ClC=1C=NNC=1 BADSZRMNXWLUKO-UHFFFAOYSA-N 0.000 description 1
JGTUBTJLRQIMAB-UHFFFAOYSA-N 4-chloro-3,5-dimethyl-1h-pyrazole Chemical compound CC1=NNC(C)=C1Cl JGTUBTJLRQIMAB-UHFFFAOYSA-N 0.000 description 1
LLNQWPTUJJYTTE-UHFFFAOYSA-N 4-iodopyrazole Chemical compound IC=1C=NNC=1 LLNQWPTUJJYTTE-UHFFFAOYSA-N 0.000 description 1
GPGKNEKFDGOXPO-UHFFFAOYSA-N 4-phenyl-1h-pyrazole Chemical compound C1=NNC=C1C1=CC=CC=C1 GPGKNEKFDGOXPO-UHFFFAOYSA-N 0.000 description 1
WVMBISZHWMJNNM-UHFFFAOYSA-N 4-propan-2-yl-1h-pyrazole Chemical compound CC(C)C=1C=NNC=1 WVMBISZHWMJNNM-UHFFFAOYSA-N 0.000 description 1
YAXKXMVDJJMGRY-UHFFFAOYSA-N 4-propyl-1h-pyrazole Chemical compound CCCC=1C=NNC=1 YAXKXMVDJJMGRY-UHFFFAOYSA-N 0.000 description 1
AKTHZWMYNACDDW-UHFFFAOYSA-N 5-chloro-2h-tetrazole Chemical compound ClC1=NN=NN1 AKTHZWMYNACDDW-UHFFFAOYSA-N 0.000 description 1
XZGLNCKSNVGDNX-UHFFFAOYSA-N 5-methyl-2h-tetrazole Chemical compound CC=1N=NNN=1 XZGLNCKSNVGDNX-UHFFFAOYSA-N 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
239000002253 acid Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000005529 alkyleneoxy group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
150000003931 anilides Chemical class 0.000 description 1
238000010923 batch production Methods 0.000 description 1
JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 1
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
239000013078 crystal Substances 0.000 description 1
BLHUAXIDWCQEPL-UHFFFAOYSA-M dibenzyl(dimethyl)azanium;methyl sulfate Chemical compound COS([O-])(=O)=O.C=1C=CC=CC=1C[N+](C)(C)CC1=CC=CC=C1 BLHUAXIDWCQEPL-UHFFFAOYSA-M 0.000 description 1
150000004816 dichlorobenzenes Chemical class 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
AKDNDOBRFDICST-UHFFFAOYSA-N methylazanium;methyl sulfate Chemical compound [NH3+]C.COS([O-])(=O)=O AKDNDOBRFDICST-UHFFFAOYSA-N 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
239000000203 mixture Substances 0.000 description 1
YHBCVAMIJFBZIY-UHFFFAOYSA-N n-phenyl-2-(1h-pyrrol-2-yl)acetamide Chemical compound C=1C=CC=CC=1NC(=O)CC1=CC=CN1 YHBCVAMIJFBZIY-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
150000003217 pyrazoles Chemical class 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
150000004023 quaternary phosphonium compounds Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
XKFPGUWSSPXXMF-UHFFFAOYSA-N tributyl(methyl)phosphanium Chemical compound CCCC[P+](C)(CCCC)CCCC XKFPGUWSSPXXMF-UHFFFAOYSA-N 0.000 description 1
SDSMZSUWTYFEBO-UHFFFAOYSA-M tributyl(methyl)phosphanium;bromide Chemical compound [Br-].CCCC[P+](C)(CCCC)CCCC SDSMZSUWTYFEBO-UHFFFAOYSA-M 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/68—Halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD79214273A 1978-07-13 1979-07-11 Verfahren zur herstellung von acetaniliden DD144771A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19782830764 DE2830764A1 (de)	1978-07-13	1978-07-13	Acetanilide

Publications (1)

Publication Number	Publication Date
DD144771A5 true DD144771A5 (de)	1980-11-05

Family

ID=6044263

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79214273A DD144771A5 (de)	1978-07-13	1979-07-11	Verfahren zur herstellung von acetaniliden

Country Status (14)

Country	Link
US (1)	US4321395A (cs)
EP (1)	EP0007080B1 (cs)
JP (1)	JPS5513283A (cs)
AR (1)	AR221732A1 (cs)
AT (1)	ATE125T1 (cs)
BR (1)	BR7904345A (cs)
CS (1)	CS208785B2 (cs)
DD (1)	DD144771A5 (cs)
DE (2)	DE2830764A1 (cs)
DK (1)	DK292779A (cs)
HU (1)	HU180423B (cs)
IL (1)	IL57350A (cs)
PL (1)	PL114229B2 (cs)
ZA (1)	ZA793511B (cs)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2854598A1 (de) *	1978-12-18	1980-07-03	Basf Ag	N-substituierte carbonsaeureanilide, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
DE3205682A1 (de) *	1982-02-17	1983-09-01	Consortium für elektrochemische Industrie GmbH, 8000 München	Azolyl-pyrrolidinone, verfahren zu deren herstellung und ihre verwendung als fungizide
US5250503A (en) *	1989-07-29	1993-10-05	Basf Aktiengesellschaft	Monoclinic metazachlor and composition
DE3925253A1 (de) *	1989-07-29	1991-01-31	Basf Ag	Monoklines metazachlor und verfahren zu seiner herstellung
DE4436293A1 (de)	1994-10-11	1996-04-18	Basf Ag	Stabile Mischung, welche Wasser und Metazachlor enthält
WO2008013984A2 (en) *	2006-07-27	2008-01-31	University Of Florida Research Foundation, Inc.	Compositions and methods for treating or preventing ophthalmic disease
AU2007277035A1 (en) *	2006-07-27	2008-01-31	University Of Florida Research Foundation, Inc.	Compositions and methods for treating or preventing ophthalmic light toxicity
AU2007277032A1 (en) *	2006-07-27	2008-01-31	University Of Florida Research Foundation, Inc.	Opsin stabilizing compounds and methods of use
IN2012DN00352A (cs) *	2009-06-16	2015-08-21	Bikam Pharmaceuticals Inc
EP2802566B1 (en)	2012-01-13	2016-03-16	Basf Se	Process for preparing acetanilides
CN104926727B (zh) *	2015-07-15	2017-09-19	江苏蓝丰生物化工股份有限公司	吡唑草胺的制备方法
GB201911300D0 (en)	2019-08-07	2019-09-18	Johnson Matthey Plc	Molecular complexes

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3004959A (en) *	1959-09-30	1961-10-17	William G Finnegan	Polymers of substituted tetrazoles
BR6465079D0 (pt) *	1963-12-09	1973-08-07	Monsanto Co	Composicoes herbicidas e processo para a preparacao de acetanilidas herbicidas
GB1227144A (cs)	1967-04-05	1971-04-07
US3442945A (en) *	1967-05-22	1969-05-06	Monsanto Co	Phytotoxic alpha-halo-acetanilides
US3637847A (en) *	1969-09-03	1972-01-25	Monsanto Co	N-haloalkyl-anilides
DE2648008C3 (de) *	1976-10-23	1980-09-04	Basf Ag, 6700 Ludwigshafen	Acetanilide
DE2704281A1 (de) *	1977-02-02	1978-08-03	Bayer Ag	N-substituierte halogenacetanilide, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide
DE2744396A1 (de) *	1977-10-03	1979-04-12	Basf Ag	Acetanilide

1978
- 1978-07-13 DE DE19782830764 patent/DE2830764A1/de not_active Withdrawn
1979
- 1979-05-18 US US06/040,224 patent/US4321395A/en not_active Expired - Lifetime
- 1979-05-21 IL IL57350A patent/IL57350A/xx unknown
- 1979-06-26 AR AR277057A patent/AR221732A1/es active
- 1979-07-06 JP JP8512079A patent/JPS5513283A/ja active Pending
- 1979-07-09 DE DE7979102314T patent/DE2960536D1/de not_active Expired
- 1979-07-09 EP EP79102314A patent/EP0007080B1/de not_active Expired
- 1979-07-09 BR BR7904345A patent/BR7904345A/pt unknown
- 1979-07-09 AT AT79102314T patent/ATE125T1/de active
- 1979-07-10 CS CS794827A patent/CS208785B2/cs unknown
- 1979-07-11 DD DD79214273A patent/DD144771A5/de unknown
- 1979-07-11 PL PL1979217028A patent/PL114229B2/xx unknown
- 1979-07-12 ZA ZA00793511A patent/ZA793511B/xx unknown
- 1979-07-12 HU HU79BA3810A patent/HU180423B/hu unknown
- 1979-07-12 DK DK292779A patent/DK292779A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
DE2960536D1 (en)	1981-10-29
IL57350A0 (en)	1979-09-30
IL57350A (en)	1982-09-30
CS208785B2 (en)	1981-09-15
ATE125T1 (de)	1981-08-15
PL114229B2 (en)	1981-01-31
BR7904345A (pt)	1980-04-08
EP0007080A1 (de)	1980-01-23
AR221732A1 (es)	1981-03-13
US4321395A (en)	1982-03-23
PL217028A1 (cs)	1980-05-19
DK292779A (da)	1980-01-14
ZA793511B (en)	1980-08-27
DE2830764A1 (de)	1980-01-31
HU180423B (en)	1983-03-28
EP0007080B1 (de)	1981-07-29
JPS5513283A (en)	1980-01-30

Publication	Publication Date	Title
DE3315681A1 (de)	1984-10-31	Verfahren zur herstellung von oxiranen
DD144771A5 (de)	1980-11-05	Verfahren zur herstellung von acetaniliden
EP0000752A2 (de)	1979-02-21	Alpha-azolysulfide, -sulfoxide und -sulfone, deren Salze und Metallkomplexe, Verfahren zu ihrer Herstellung, sowie sie enthaltende Mittel zur Pilzbekämpfung
EP0192055B1 (de)	1989-08-09	Hydroxyalkinyl-azolyl-Derivate, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide
EP0121171B1 (de)	1989-05-10	Fungizide Mittel, Verfahren zu ihrer Herstellung und deren Verwendung
DE2720949A1 (de)	1978-11-23	Azolylaether-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
DE3325313A1 (de)	1985-01-31	Fungizide mittel, deren herstellung und verwendung
EP0017080A2 (de)	1980-10-15	Verfahren zur Herstellung von Hydroxyethyl-azolen; Zwischenprodukte
EP0008057A1 (de)	1980-02-20	Verfahren zur Herstellung von N-substituierten alpha-Halogen-acetaniliden
DE2334352C3 (de)	1981-10-01	Im Heterocyclus halogenierte 1-(1,2,4-Triazol-1-yl)-1-phenoxy-3,3-dimethyl-butan-2-on- Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide
EP0027177B1 (de)	1984-05-02	1-Azolyl-1-halogen-alkan-2-one und Verfahren zur Herstellung von 1-Azolyl-1-phenoxy-alkan-2-onen
DD213825A5 (de)	1984-09-26	Pflanzenschutzmittel
EP0057864B1 (de)	1984-10-03	2-Azolylmethyl-1,3-dioxolan- und -dioxan-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide
EP0082400B1 (de)	1991-03-06	Fungizide alpha-Azolylglykole
DE2401715C3 (de)	1981-10-22	Verfahren zur Herstellung von 1-(1,2,4-Triazol-1-yl)-1-phenoxy-3,3-dimethyl-butan-2-on-Derivaten
EP0141204B1 (de)	1990-05-02	Hydroxyethyl-azol-Derivate
EP0129170B1 (de)	1990-01-10	Triazolyl-ketonoxime und -dioxime, Verfahren zu ihrer Herstellung und ihre Verwendung als Pflanzenwachstumsregulatoren
IE48786B1 (en)	1985-05-15	Imidazolyl oxime ether compositions
DE3413363A1 (de)	1985-10-17	Benzofuran-2-yl-ethyl-imidazolderivate, verfahren zu ihrer herstellung und pharmazeutische mittel
DE1940627A1 (de)	1971-02-11	Verfahren zur Herstellung von N-Tritylimidazolen und -triazolen
DE2954650C2 (en)	1990-07-26	2-Aryl-2-hydroxyethyl-imidazole and -triazole derivs. prepn.
EP0110116A2 (de)	1984-06-13	Verfahren zur Herstellung von Keten-O,N-acetalen
DE3119390A1 (de)	1982-12-09	3-substituierte 1-azolyl-3-methyl-1-phenoxy-butan-2-one und -ole, verfahren zu iher herstellung und ihre verwendung als fungizide
DE3539993A1 (de)	1987-05-14	Verfahren zur herstellung von (beta)-hydroxyethyl-azol-derivaten
DE2106845A1 (en)	1972-08-31	2,3-di-heteroaromatic-substd 1,4-quinones - with herbicidal and fungicidal activity