DE2008677A1 - Verfahren zur Herstellung von 5-Formamidinopyrazol-4-aldehyden - Google Patents
Verfahren zur Herstellung von 5-Formamidinopyrazol-4-aldehydenInfo
- Publication number
- DE2008677A1 DE2008677A1 DE19702008677 DE2008677A DE2008677A1 DE 2008677 A1 DE2008677 A1 DE 2008677A1 DE 19702008677 DE19702008677 DE 19702008677 DE 2008677 A DE2008677 A DE 2008677A DE 2008677 A1 DE2008677 A1 DE 2008677A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- radical
- nitrogen atom
- general formula
- pyrazole
- 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 9
- 238000002360 preparation method Methods 0.000 title claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- -1 araliphatic Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
- 239000007858 starting material Substances 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CJDYNUBRSBSSJU-UHFFFAOYSA-N 2-benzylpyrazol-3-amine Chemical compound NC1=CC=NN1CC1=CC=CC=C1 CJDYNUBRSBSSJU-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 2
- LRGBDJBDJXZTTD-UHFFFAOYSA-N 1h-pyrazole-4-carbaldehyde Chemical compound O=CC=1C=NNC=1 LRGBDJBDJXZTTD-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- NQYSFJUBWFLIMB-UHFFFAOYSA-N 2-[(2,4-dichlorophenyl)methyl]pyrazol-3-amine Chemical compound NC1=CC=NN1CC1=CC=C(Cl)C=C1Cl NQYSFJUBWFLIMB-UHFFFAOYSA-N 0.000 description 2
- OMPYFUBKXQUIGG-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]pyrazol-3-amine Chemical compound NC1=CC=NN1CC1=CC=CC=C1Cl OMPYFUBKXQUIGG-UHFFFAOYSA-N 0.000 description 2
- NDPAXNCKZIOPJZ-UHFFFAOYSA-N 2-[(2-methoxyphenyl)methyl]pyrazol-3-amine Chemical compound COC1=CC=CC=C1CN1C(N)=CC=N1 NDPAXNCKZIOPJZ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- GTCCMGFBIWUBLQ-UHFFFAOYSA-N formamide;hydrochloride Chemical compound Cl.NC=O GTCCMGFBIWUBLQ-UHFFFAOYSA-N 0.000 description 2
- 150000003948 formamides Chemical class 0.000 description 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- UTACNSITJSJFHA-UHFFFAOYSA-N 1,1,1,3-tetrachloropropane Chemical compound ClCCC(Cl)(Cl)Cl UTACNSITJSJFHA-UHFFFAOYSA-N 0.000 description 1
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- IYXYXQGSWRTPHX-UHFFFAOYSA-N 2-(4-chlorophenyl)pyrazol-3-amine Chemical compound NC1=CC=NN1C1=CC=C(Cl)C=C1 IYXYXQGSWRTPHX-UHFFFAOYSA-N 0.000 description 1
- RBBUZPGMZQSXCP-UHFFFAOYSA-N 2-[(2,6-dichlorophenyl)methyl]pyrazol-3-amine Chemical compound NC1=CC=NN1CC1=C(Cl)C=CC=C1Cl RBBUZPGMZQSXCP-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- XOSDYLFXPMFRGF-UHFFFAOYSA-N 2-methyl-5-nitrobenzonitrile Chemical compound CC1=CC=C([N+]([O-])=O)C=C1C#N XOSDYLFXPMFRGF-UHFFFAOYSA-N 0.000 description 1
- JESRNIJXVIFVOV-UHFFFAOYSA-N 2-methylpyrazol-3-amine Chemical compound CN1N=CC=C1N JESRNIJXVIFVOV-UHFFFAOYSA-N 0.000 description 1
- BTOJSYRZQZOMOK-UHFFFAOYSA-N 4-chloro-7-(4-methylphenyl)sulfonylpyrrolo[2,3-d]pyrimidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=NC(Cl)=C2C=C1 BTOJSYRZQZOMOK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- CDZDPHPSWKHONZ-UHFFFAOYSA-N hypochlorous acid;phosphane Chemical compound P.ClO CDZDPHPSWKHONZ-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- PEWAOAOTRFUILG-UHFFFAOYSA-N imidazolidine-1-carbaldehyde Chemical compound O=CN1CCNC1 PEWAOAOTRFUILG-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 239000008096 xylene Substances 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
- C07D231/14—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
- C07D231/38—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702008677 DE2008677A1 (de) | 1970-02-25 | 1970-02-25 | Verfahren zur Herstellung von 5-Formamidinopyrazol-4-aldehyden |
| CH93271A CH547287A (de) | 1970-02-25 | 1971-01-21 | Verfahren zur herstellung von 5-formamidino-pyrazol-4aldehyden. |
| FR7105735A FR2078838A5 (cg-RX-API-DMAC10.html) | 1970-02-25 | 1971-02-19 | |
| BE763305A BE763305A (fr) | 1970-02-25 | 1971-02-23 | Procede de preparation de 5-formamidino-pyrazol-4-aldehydes |
| GB2251171A GB1330059A (en) | 1970-02-25 | 1971-04-19 | 5-formamidinopyrazole-4-aldehydes and their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702008677 DE2008677A1 (de) | 1970-02-25 | 1970-02-25 | Verfahren zur Herstellung von 5-Formamidinopyrazol-4-aldehyden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2008677A1 true DE2008677A1 (de) | 1971-09-16 |
Family
ID=5763274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702008677 Pending DE2008677A1 (de) | 1970-02-25 | 1970-02-25 | Verfahren zur Herstellung von 5-Formamidinopyrazol-4-aldehyden |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE763305A (cg-RX-API-DMAC10.html) |
| CH (1) | CH547287A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2008677A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2078838A5 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1330059A (cg-RX-API-DMAC10.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995027700A1 (en) * | 1994-04-08 | 1995-10-19 | Sumitomo Chemical Company, Limited | Ether compound, use thereof, and intermediate for producing the compound |
-
1970
- 1970-02-25 DE DE19702008677 patent/DE2008677A1/de active Pending
-
1971
- 1971-01-21 CH CH93271A patent/CH547287A/xx not_active IP Right Cessation
- 1971-02-19 FR FR7105735A patent/FR2078838A5/fr not_active Expired
- 1971-02-23 BE BE763305A patent/BE763305A/xx unknown
- 1971-04-19 GB GB2251171A patent/GB1330059A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995027700A1 (en) * | 1994-04-08 | 1995-10-19 | Sumitomo Chemical Company, Limited | Ether compound, use thereof, and intermediate for producing the compound |
| US5684022A (en) * | 1994-04-08 | 1997-11-04 | Sumitomo Chemical Company, Limited | Ether compounds, their use, and intermediates for use in their production |
| AU684352B2 (en) * | 1994-04-08 | 1997-12-11 | Sumitomo Chemical Company, Limited | Ether compound, use thereof, and intermediate for producing the compound |
| RU2139279C1 (ru) * | 1994-04-08 | 1999-10-10 | Сумитомо Кемикал Компани, Лимитед | Производные простого эфира, средство для борьбы с насекомыми и соединение фенола |
Also Published As
| Publication number | Publication date |
|---|---|
| BE763305A (fr) | 1971-08-23 |
| GB1330059A (en) | 1973-09-12 |
| CH547287A (de) | 1974-03-29 |
| FR2078838A5 (cg-RX-API-DMAC10.html) | 1971-11-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2105687A1 (de) | Verfahren zur Herstellung von 2,1,3-Benzothiadiazin-4-on-2,2-dioxiden | |
| DE3011809A1 (de) | Pyrimidyl-chinazoline, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische praeparate und ihre verwendung | |
| DE2008677A1 (de) | Verfahren zur Herstellung von 5-Formamidinopyrazol-4-aldehyden | |
| DE1237580B (de) | Verfahren zur Herstellung von in 1-Stellung substituierten 3-Phenylamino-2-pyrazolin-5-onen | |
| DE2056173A1 (de) | 3,5 Diphenyl 4 pyrazolessigsaure. ihre m 1 Stellung substituierten Derivate und Verfahren zur Herstellung dieser Verbin düngen | |
| DE2025427A1 (en) | 2,6-dihydroxy-3-oxo-pyridine cpds prodn- from 2,6-dihydroxy cpds, - starting materials for dyes and pesticides | |
| DE1950600A1 (de) | Verfahren zur Herstellung von Benzimidazoisochinolon-aldehyden | |
| DE1912941A1 (de) | Verfahren zur Herstellung von 6-Alkoxy-Pyridaziniumverbindungen | |
| DE2115625A1 (cg-RX-API-DMAC10.html) | ||
| DE2604727A1 (de) | 1-arylmethyl-2-imidazolidinone | |
| DE1445952A1 (de) | Verfahren zur Herstellung von heterocyclischen Verbindungen | |
| DE1668034A1 (de) | Verfahren zur Herstellung von Benzylcyaniden und deren Homologen | |
| DE2413281C2 (de) | Cumarinverbindungen | |
| DE2153356A1 (de) | Verfahren zur Herstellung von alpha Amlinocarbonsauren und ihren Derivaten | |
| DE2329653A1 (de) | Neue 5-nitrofuran-verbindungen | |
| DE2013261A1 (de) | Verfahren zur Herstellung von Furanen | |
| DE1945053C3 (de) | Basische Farbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben, Bedrucken und Massefärben von Polyacrylnitril, sauer modifizierten Polyestern oder modifizierten Polyamiden | |
| DE1941861A1 (de) | Verfahren zur Herstellung von Bezimidazo-isochinolonen | |
| DE2104682C3 (de) | Verfahren zur Herstellung von o-Sulfamidobenzoesäuren | |
| DE1569674C (de) | Styrylfarbstoffe | |
| DE1543941C (de) | Verfahren zur Herstellung von 1-Oxa-2-methyl-3-aminocarbonyl-4-thia-cyclohex-2-en-4-oxiden oder 4,4-dioxiden | |
| DE1695225A1 (de) | Verfahren zur Herstellung von Benzodiazepin-Derivaten | |
| DE2310185A1 (de) | Verfahren zur herstellung von isoxazol | |
| DE2016691A1 (de) | Verfahren zur Herstellung von 6-Chlorpyridaziniumverbindungen | |
| DE1670967A1 (de) | Verfahren zur Herstellung von 3-Imino-1,2-benzisothiazolinen |