DE2221812A1 - Verfahren zur herstellung von thiosemicarbaziden - Google Patents
Verfahren zur herstellung von thiosemicarbazidenInfo
- Publication number
- DE2221812A1 DE2221812A1 DE19722221812 DE2221812A DE2221812A1 DE 2221812 A1 DE2221812 A1 DE 2221812A1 DE 19722221812 DE19722221812 DE 19722221812 DE 2221812 A DE2221812 A DE 2221812A DE 2221812 A1 DE2221812 A1 DE 2221812A1
- Authority
- DE
- Germany
- Prior art keywords
- thiosemicarbazide
- tert
- reaction
- butyl
- sulfuric acid
- 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 15
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 28
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 24
- -1 alkylmerca.pto Chemical group 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 16
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 150000003583 thiosemicarbazides Chemical class 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 7
- MUQNAPSBHXFMHT-UHFFFAOYSA-N tert-butylhydrazine Chemical compound CC(C)(C)NN MUQNAPSBHXFMHT-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- PTVZQOAHCSKAAS-UHFFFAOYSA-N 4-methyl-3-thiosemicarbazide Chemical compound CNC(=S)NN PTVZQOAHCSKAAS-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- NXUFEELLNJFGQV-UHFFFAOYSA-N (tert-butylamino)thiourea Chemical class CC(C)(C)NNC(N)=S NXUFEELLNJFGQV-UHFFFAOYSA-N 0.000 description 2
- RGQBZKIOJAFDQB-UHFFFAOYSA-N 1-(tert-butylamino)-3-methylthiourea Chemical compound CNC(=S)NNC(C)(C)C RGQBZKIOJAFDQB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- COEWIOVAZWGZBG-UHFFFAOYSA-N aminocarbamothioic s-acid Chemical compound NNC(O)=S COEWIOVAZWGZBG-UHFFFAOYSA-N 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- YRQHNWRBJAFICQ-UHFFFAOYSA-N butylaminothiourea Chemical class CCCCNNC(N)=S YRQHNWRBJAFICQ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000008164 mustard oil Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- AMGVTOGESVKINO-UHFFFAOYSA-N 1-amino-3-dodecylthiourea Chemical compound CCCCCCCCCCCCNC(=S)NN AMGVTOGESVKINO-UHFFFAOYSA-N 0.000 description 1
- WMFXGKCDSJXKHO-UHFFFAOYSA-N 1-amino-3-propan-2-ylthiourea Chemical compound CC(C)NC(=S)NN WMFXGKCDSJXKHO-UHFFFAOYSA-N 0.000 description 1
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 1
- PFLUPZGCTVGDLV-UHFFFAOYSA-N acetone azine Chemical compound CC(C)=NN=C(C)C PFLUPZGCTVGDLV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000006208 butylation Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- QKSQWQOAUQFORH-VAWYXSNFSA-N tert-butyl (ne)-n-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate Chemical compound CC(C)(C)OC(=O)\N=N\C(=O)OC(C)(C)C QKSQWQOAUQFORH-VAWYXSNFSA-N 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 230000006209 tert-butylation Effects 0.000 description 1
- 150000003559 thiocarbamic acid halides Chemical class 0.000 description 1
- 150000003560 thiocarbamic acids Chemical class 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C337/00—Derivatives of thiocarbonic acids containing functional groups covered by groups C07C333/00 or C07C335/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C337/06—Compounds containing any of the groups, e.g. thiosemicarbazides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722221812 DE2221812A1 (de) | 1972-05-04 | 1972-05-04 | Verfahren zur herstellung von thiosemicarbaziden |
| IL42151A IL42151A (en) | 1972-05-04 | 1973-05-01 | The production of 1-tert-butyl thiosemicarbazides |
| US356694A US3907887A (en) | 1972-05-04 | 1973-05-02 | Process for the preparation of 1-tert.-butyl-thiosemicarbazide compounds |
| IT23629/73A IT988643B (it) | 1972-05-04 | 1973-05-02 | Processo per la produzione di tiosemicarbazidi |
| CH626173A CH577964A5 (en:Method) | 1972-05-04 | 1973-05-02 | |
| BE130690A BE799035A (fr) | 1972-05-04 | 1973-05-03 | Procede de preparation de thiosemicarbazides, |
| BR3189/73A BR7303189D0 (pt) | 1972-05-04 | 1973-05-03 | Processo para a preparacao de tio-semicarbazidas |
| GB2107773A GB1382974A (en) | 1972-05-04 | 1973-05-03 | Process for the production of thiosemicarbazides |
| FR7316085A FR2183258B1 (en:Method) | 1972-05-04 | 1973-05-04 | |
| NL7306263A NL7306263A (en:Method) | 1972-05-04 | 1973-05-04 | |
| JP48049174A JPS4954333A (en:Method) | 1972-05-04 | 1973-05-04 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722221812 DE2221812A1 (de) | 1972-05-04 | 1972-05-04 | Verfahren zur herstellung von thiosemicarbaziden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2221812A1 true DE2221812A1 (de) | 1973-11-15 |
Family
ID=5844030
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722221812 Pending DE2221812A1 (de) | 1972-05-04 | 1972-05-04 | Verfahren zur herstellung von thiosemicarbaziden |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3907887A (en:Method) |
| JP (1) | JPS4954333A (en:Method) |
| BE (1) | BE799035A (en:Method) |
| BR (1) | BR7303189D0 (en:Method) |
| CH (1) | CH577964A5 (en:Method) |
| DE (1) | DE2221812A1 (en:Method) |
| FR (1) | FR2183258B1 (en:Method) |
| GB (1) | GB1382974A (en:Method) |
| IL (1) | IL42151A (en:Method) |
| IT (1) | IT988643B (en:Method) |
| NL (1) | NL7306263A (en:Method) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3483308D1 (de) * | 1983-11-21 | 1990-10-31 | Fujisawa Pharmaceutical Co | Semicarbazid-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zusammensetzungen. |
| US4694004A (en) * | 1984-07-09 | 1987-09-15 | Fujisawa Pharmaceutical Co., Ltd. | Semicarbazide derivatives, processes for preparation thereof and pharmaceutical composition comprising the same |
-
1972
- 1972-05-04 DE DE19722221812 patent/DE2221812A1/de active Pending
-
1973
- 1973-05-01 IL IL42151A patent/IL42151A/en unknown
- 1973-05-02 US US356694A patent/US3907887A/en not_active Expired - Lifetime
- 1973-05-02 CH CH626173A patent/CH577964A5/xx not_active IP Right Cessation
- 1973-05-02 IT IT23629/73A patent/IT988643B/it active
- 1973-05-03 GB GB2107773A patent/GB1382974A/en not_active Expired
- 1973-05-03 BE BE130690A patent/BE799035A/xx unknown
- 1973-05-03 BR BR3189/73A patent/BR7303189D0/pt unknown
- 1973-05-04 NL NL7306263A patent/NL7306263A/xx unknown
- 1973-05-04 FR FR7316085A patent/FR2183258B1/fr not_active Expired
- 1973-05-04 JP JP48049174A patent/JPS4954333A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL7306263A (en:Method) | 1973-11-06 |
| IL42151A0 (en) | 1973-07-30 |
| CH577964A5 (en:Method) | 1976-07-30 |
| IT988643B (it) | 1975-04-30 |
| FR2183258B1 (en:Method) | 1977-02-11 |
| IL42151A (en) | 1976-04-30 |
| BE799035A (fr) | 1973-11-05 |
| FR2183258A1 (en:Method) | 1973-12-14 |
| JPS4954333A (en:Method) | 1974-05-27 |
| US3907887A (en) | 1975-09-23 |
| BR7303189D0 (pt) | 1974-07-18 |
| GB1382974A (en) | 1975-02-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1470082C3 (de) | Verfahren zur Herstellung von in der 2-Stellung substituierten Benzimidazolen | |
| DE1695186B2 (de) | 2-nitro-1-imidazolylessigsaeurebenzylamid | |
| DE69603261T2 (de) | Verfahren zur herstellung von 1,2-benzisothiazolonen | |
| DE2221812A1 (de) | Verfahren zur herstellung von thiosemicarbaziden | |
| DE941288C (de) | Verfahren zur Herstellung substituierter 2-Imino-4-thiazoline oder von Salzen derselben bzw. von substituierten 2-Aminothiazolen | |
| DE915809C (de) | Verfahren zur Herstellung von heterocyclischen Sulfonamiden | |
| DD249479A5 (de) | Verfahren zur herstellung von propionamidin-derivaten | |
| DE2166270C3 (de) | Nicotinoylaminoäthansulfonyl-2amino-thiazol | |
| DE1670937B2 (de) | 2-Halogenmethyl-3-carbonsäureamidochinoxalin-di-N-oxide-0.4) | |
| DE2512702C2 (de) | Substituierte 1-Amino-3-phenyl-indole, deren Salze und Verfahren zu ihrer Herstellung | |
| CH500221A (de) | Verfahren zur Herstellung von N-disubstituierten 3-Amino-1,2-benzisothiazol-Derivaten | |
| DE2942677A1 (de) | Verfahren zur herstellung von neuen sulfonsaeurecycloalkylamiden und ihre mikrobizide verwendung | |
| DE1643797A1 (de) | Neue Thionocarbamidsaeureester und Verfahren zu ihrer Herstellung | |
| AT375346B (de) | Verfahren zur herstellung von neuen substituierten 1-benzoyl-2-phenylimino-imidazolidinen und von deren salzen | |
| DE2033611C3 (de) | Verfahren zur Herstellung von 1-(2-Thiazolyl)-2-oxotetrahydroimidazol | |
| DE2304587A1 (de) | Beta-amino-beta-imino-propionsaeureester | |
| DE1470163C (de) | Verfahren zur Herstellung von 3,3Äthylenbis-(tetrahydro-4,6-dimethyl-2Hl,3,5-thiadiazin-2-thion) | |
| AT373588B (de) | Verfahren zur herstellung von neuen substituierten 1-benzoyl-2-phenylimino-imidazolidinen und von deren salzen | |
| CH364795A (de) | Verfahren zur Herstellung quaternärer Ammoniumsalze | |
| DE1768130C3 (de) | lsocyan-diphenyl(-thio)-äther sowie Verfahren zu ihrer Herstellung und deren Verwendung zur Bekämpfung von Akariden | |
| DE2011026C (de) | S-Carboxy-öJ-dimethoxy-1 -thiaisochroman-1,1-dioxide und Verfahren zu ihrer Herstellung | |
| DE1770772A1 (de) | Verfahren zur Herstellung von Pyridazoniminen | |
| DE2250911A1 (de) | Phenylguanidin-derivate, ein verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel | |
| DE2306112A1 (de) | Thioharnstoffderivate der vitamin-asaeure | |
| DE3324399A1 (de) | Verfahren zur herstellung von 2-alkylsulfonylalkylenpyrimidinen |