DE1810821A1 - Verfahren zum Herstellen halogenierter Salicylanilide - Google Patents
Verfahren zum Herstellen halogenierter SalicylanilideInfo
- Publication number
- DE1810821A1 DE1810821A1 DE19681810821 DE1810821A DE1810821A1 DE 1810821 A1 DE1810821 A1 DE 1810821A1 DE 19681810821 DE19681810821 DE 19681810821 DE 1810821 A DE1810821 A DE 1810821A DE 1810821 A1 DE1810821 A1 DE 1810821A1
- Authority
- DE
- Germany
- Prior art keywords
- salicylanilide
- iodine
- bromine
- chloro
- chlorine
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 31
- 229950000975 salicylanilide Drugs 0.000 claims description 27
- -1 trifluoromethylphenoxy Chemical group 0.000 claims description 22
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 239000011630 iodine Substances 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000003931 anilides Chemical class 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 4
- 230000026030 halogenation Effects 0.000 claims description 4
- 238000005658 halogenation reaction Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 4
- OBFIGGGJNMHDKD-UHFFFAOYSA-N 2-(4-chlorophenyl)peroxy-N-phenylbenzamide Chemical compound ClC1=CC=C(OOC=2C(C(=O)NC3=CC=CC=C3)=CC=CC2)C=C1 OBFIGGGJNMHDKD-UHFFFAOYSA-N 0.000 claims 1
- 235000013405 beer Nutrition 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 17
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- 229960004889 salicylic acid Drugs 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000026045 iodination Effects 0.000 description 3
- 238000006192 iodination reaction Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000545744 Hirudinea Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 208000030852 Parasitic disease Diseases 0.000 description 2
- 230000000507 anthelmentic effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 2
- 150000002496 iodine Chemical class 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- ZEMAAAKSMFAZIM-UHFFFAOYSA-N n-phenylsulfanylaniline Chemical compound C=1C=CC=CC=1NSC1=CC=CC=C1 ZEMAAAKSMFAZIM-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003872 salicylic acid derivatives Chemical class 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
- URUJZHZLCCIILC-UHFFFAOYSA-N 1-chloro-4-(4-chlorophenoxy)benzene Chemical compound C1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1 URUJZHZLCCIILC-UHFFFAOYSA-N 0.000 description 1
- ZIDYALDTDUSPFJ-UHFFFAOYSA-N 2-chloro-4-nitro-1-phenoxybenzene Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC=C1 ZIDYALDTDUSPFJ-UHFFFAOYSA-N 0.000 description 1
- JKIFPWHZEZQCQA-UHFFFAOYSA-N 2-nitrobenzenethiol Chemical compound [O-][N+](=O)C1=CC=CC=C1S JKIFPWHZEZQCQA-UHFFFAOYSA-N 0.000 description 1
- ZKFZVCBUFBFPSJ-UHFFFAOYSA-N 3-chloro-4-(3-methoxyphenoxy)aniline Chemical compound COC1=CC=CC(OC=2C(=CC(N)=CC=2)Cl)=C1 ZKFZVCBUFBFPSJ-UHFFFAOYSA-N 0.000 description 1
- WTPFYPUXUHYGIP-UHFFFAOYSA-N 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline Chemical compound ClC1=CC(N)=CC=C1OC1=CC=CC(C(F)(F)F)=C1 WTPFYPUXUHYGIP-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- 241000415078 Anemone hepatica Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- PMLSTCYISWIHAC-UHFFFAOYSA-N ClC=1C=C(NC(C=2C(O)=CC=CC2)=O)C=CC1OC1=CC=C(C=C1)OC Chemical compound ClC=1C=C(NC(C=2C(O)=CC=CC2)=O)C=CC1OC1=CC=C(C=C1)OC PMLSTCYISWIHAC-UHFFFAOYSA-N 0.000 description 1
- 241000242711 Fasciola hepatica Species 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- LUKVWSUSIKQSBE-UHFFFAOYSA-N N-[2-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl]-2-hydroxybenzamide Chemical compound ClC1=C(NC(C=2C(O)=CC=CC2)=O)C=CC(=C1)OC1=CC(=CC=C1)C(F)(F)F LUKVWSUSIKQSBE-UHFFFAOYSA-N 0.000 description 1
- 208000000291 Nematode infections Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 241000242541 Trematoda Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- UYPAJBPYDFUMSN-UHFFFAOYSA-N [2-(phenylcarbamoyl)phenyl] hypoiodite Chemical compound IOC=1C(C(=O)NC2=CC=CC=C2)=CC=CC=1 UYPAJBPYDFUMSN-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000006011 chloroethoxy group Chemical group 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 208000006275 fascioliasis Diseases 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000002497 iodine compounds Chemical group 0.000 description 1
- CBEQRNSPHCCXSH-UHFFFAOYSA-N iodine monobromide Chemical compound IBr CBEQRNSPHCCXSH-UHFFFAOYSA-N 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 150000002843 nonmetals Chemical group 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 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
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04C—STRUCTURAL ELEMENTS; BUILDING MATERIALS
- E04C5/00—Reinforcing elements, e.g. for concrete; Auxiliary elements therefor
- E04C5/16—Auxiliary parts for reinforcements, e.g. connectors, spacers, stirrups
- E04C5/18—Spacers of metal or substantially of metal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68712867A | 1967-12-01 | 1967-12-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1810821A1 true DE1810821A1 (de) | 1969-07-17 |
Family
ID=24759178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681810821 Pending DE1810821A1 (de) | 1967-12-01 | 1968-11-25 | Verfahren zum Herstellen halogenierter Salicylanilide |
Country Status (12)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2526986A1 (de) * | 1974-06-19 | 1976-01-08 | Merck & Co Inc | Waessrige rafoxanidpraeparate |
-
1968
- 1968-11-14 NL NL6816239A patent/NL6816239A/xx unknown
- 1968-11-19 IL IL31105A patent/IL31105A/en unknown
- 1968-11-22 ES ES360542A patent/ES360542A1/es not_active Expired
- 1968-11-25 DE DE19681810821 patent/DE1810821A1/de active Pending
- 1968-11-25 GB GB55818/68A patent/GB1212628A/en not_active Expired
- 1968-11-26 YU YU2768/68A patent/YU32305B/xx unknown
- 1968-11-27 AT AT1155268A patent/AT293363B/de not_active IP Right Cessation
- 1968-11-27 SE SE16156/68A patent/SE368394B/xx unknown
- 1968-11-29 CH CH1782068A patent/CH526514A/de not_active IP Right Cessation
- 1968-11-29 NO NO4777/68A patent/NO122313B/no unknown
- 1968-11-29 BR BR204469/68A patent/BR6804469D0/pt unknown
- 1968-12-02 CS CS688206A patent/CS149651B2/cs unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2526986A1 (de) * | 1974-06-19 | 1976-01-08 | Merck & Co Inc | Waessrige rafoxanidpraeparate |
Also Published As
| Publication number | Publication date |
|---|---|
| ES360542A1 (es) | 1970-10-16 |
| GB1212628A (en) | 1970-11-18 |
| CH526514A (de) | 1972-08-15 |
| NL6816239A (enrdf_load_stackoverflow) | 1969-06-03 |
| CS149651B2 (en) | 1973-07-25 |
| AT293363B (de) | 1971-10-11 |
| NO122313B (enrdf_load_stackoverflow) | 1971-06-14 |
| BR6804469D0 (pt) | 1973-02-22 |
| YU32305B (en) | 1974-08-31 |
| YU276868A (en) | 1974-02-28 |
| SE368394B (enrdf_load_stackoverflow) | 1974-07-01 |
| IL31105A (en) | 1972-08-30 |
| IL31105A0 (en) | 1969-01-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1418217A1 (de) | Verfahren zur Herstellung von neuen Arylsulfonarylamiden | |
| DE2223957A1 (de) | Schädlingsbekämpfungsmittel und Verfahren zur Herstellung des Wirkstoffs | |
| DE2006472A1 (de) | Furan-3-carboxamid-Derivate und Verfahren zu ihrer Herstellung | |
| DE1943799A1 (de) | Verfahren zur Alkylierung von Benzthiazolazoverbindungen | |
| DE1810821A1 (de) | Verfahren zum Herstellen halogenierter Salicylanilide | |
| DE1808679A1 (de) | Verfahren zum Herstellen von Salicylaniliden | |
| DE1618709A1 (de) | Verfahren zur Herstellung von substituierten Salicylaniliden | |
| DE1808681A1 (de) | Verfahren zum Herstellen von Salicylaniliden | |
| DE1593871A1 (de) | Verfahren zur Herstellung von Nitroaminodiarylaethern | |
| DE1518309C3 (de) | 2-Alkoxy-S-trifluormethylbenzoesäuren und Verfahren zu ihrer Herstellung | |
| DE2213607C3 (de) | Trifluormethyl-salicylanilide, Verfahren zu ihrer Herstellung und pharmazeutische Präparate, die diese Verbindungen enthalten | |
| DE2409260A1 (de) | Verfahren zur herstellung von derivaten der nikotinsaeure | |
| DE1810162A1 (de) | Phenoxy- und Phenylthiopyridine und Verfahren zu deren Herstellung | |
| DE920790C (de) | Verfahren zur Herstellung von Salicylsaeurearylamiden | |
| DE660693C (de) | Verfahren zur Herstellung von in p-Stellung zum Stickstoffatom durch die Aldehydgruppe substituierten heterocyclischen Stickstoffverbindungen | |
| DE544087C (de) | Verfahren zur Darstellung aromatischer N-Dialkylaminoalkylaminoaldehyde und ihrer Derivate | |
| DE563131C (de) | Verfahren zur Darstellung von 3, 5-Dihalogen-2-pyridon-N-alkylcarbon- und -sulfonsaeuren bzw. deren Salzen | |
| DE673174C (de) | Verfahren zur Herstellung von 4-Methyl-5-ª‰-oxyaethylthiazol | |
| DE1543185A1 (de) | Acylphenole und Verfahren zu deren Herstellung | |
| AT210877B (de) | Verfahren zur Herstellung von neuen Aminobenzoesäurederivaten | |
| AT209894B (de) | Verfahren zur Herstellung von neuen Anthranilsäurederivaten | |
| AT48028B (de) | Verfahren zur Darstellung von Halogenderivaten der Indigoreihe. | |
| DE1174768B (de) | Verfahren zur Herstellung von 4-Nitrostilbenen | |
| DE1805778B2 (de) | 2-amino-4-phenylsulfonyl-benzolsulfonamide und verfahren zur herstellung | |
| DE923064C (de) | Verfahren zur Herstellung von 7-Brom-5-chlorisatin |