DE2254701C3 - Verfahren zur Herstellung von in 2- und 5-Stellung substituierten Thiazolinen-(3) - Google Patents
Verfahren zur Herstellung von in 2- und 5-Stellung substituierten Thiazolinen-(3)Info
- Publication number
- DE2254701C3 DE2254701C3 DE2254701A DE2254701A DE2254701C3 DE 2254701 C3 DE2254701 C3 DE 2254701C3 DE 2254701 A DE2254701 A DE 2254701A DE 2254701 A DE2254701 A DE 2254701A DE 2254701 C3 DE2254701 C3 DE 2254701C3
- Authority
- DE
- Germany
- Prior art keywords
- mol
- ammonium
- reaction
- mixture
- dithio
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 11
- 150000003549 thiazolines Chemical class 0.000 title description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 13
- 229910021529 ammonia Inorganic materials 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- 150000003863 ammonium salts Chemical class 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 8
- -1 alkyl radical Chemical class 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HNGVMXJRVDXZPD-UHFFFAOYSA-N 2-methyl-2-[(2-methyl-1-oxopropan-2-yl)disulfanyl]propanal Chemical compound O=CC(C)(C)SSC(C)(C)C=O HNGVMXJRVDXZPD-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 150000001728 carbonyl compounds Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 229960001701 chloroform Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- SDNJNDFHCODQDQ-UHFFFAOYSA-N n-(2-ethylphenyl)-2-[[2-[(2-ethylphenyl)carbamoyl]phenyl]disulfanyl]benzamide Chemical compound CCC1=CC=CC=C1NC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(=O)NC1=CC=CC=C1CC SDNJNDFHCODQDQ-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- SIJKDVFQRJZHAH-UHFFFAOYSA-N 2-[(2-formylcyclododecyl)disulfanyl]cyclododecane-1-carbaldehyde Chemical compound O=CC1CCCCCCCCCCC1SSC1C(C=O)CCCCCCCCCC1 SIJKDVFQRJZHAH-UHFFFAOYSA-N 0.000 description 1
- RLZNOLCJQOFNBK-UHFFFAOYSA-N 2-[(2-formylcyclohexyl)disulfanyl]cyclohexane-1-carbaldehyde Chemical compound O=CC1CCCCC1SSC1C(C=O)CCCC1 RLZNOLCJQOFNBK-UHFFFAOYSA-N 0.000 description 1
- UZXAXASOTWRKHY-UHFFFAOYSA-N 2-[(2-formylcyclooctyl)disulfanyl]cyclooctane-1-carbaldehyde Chemical compound O=CC1CCCCCCC1SSC1C(C=O)CCCCCC1 UZXAXASOTWRKHY-UHFFFAOYSA-N 0.000 description 1
- KWIPUXXIFQQMKN-UHFFFAOYSA-N 2-azaniumyl-3-(4-cyanophenyl)propanoate Chemical compound OC(=O)C(N)CC1=CC=C(C#N)C=C1 KWIPUXXIFQQMKN-UHFFFAOYSA-N 0.000 description 1
- DMYILSIRPBVUKO-UHFFFAOYSA-N 2-methyl-2-[(2-methyl-1-oxobutan-2-yl)disulfanyl]butanal Chemical compound CCC(C)(C=O)SSC(C)(CC)C=O DMYILSIRPBVUKO-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229940090948 ammonium benzoate Drugs 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- NGPGDYLVALNKEG-UHFFFAOYSA-N azanium;azane;2,3,4-trihydroxy-4-oxobutanoate Chemical compound [NH4+].[NH4+].[O-]C(=O)C(O)C(O)C([O-])=O NGPGDYLVALNKEG-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- KIYUNVUWDQKWPJ-UHFFFAOYSA-N cyclododecanecarbaldehyde Chemical compound O=CC1CCCCCCCCCCC1 KIYUNVUWDQKWPJ-UHFFFAOYSA-N 0.000 description 1
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 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
- IGGUWVNICWZJQU-UHFFFAOYSA-N cyclooctanecarbaldehyde Chemical compound O=CC1CCCCCCC1 IGGUWVNICWZJQU-UHFFFAOYSA-N 0.000 description 1
- VELDYOPRLMJFIK-UHFFFAOYSA-N cyclopentanecarbaldehyde Chemical compound O=CC1CCCC1 VELDYOPRLMJFIK-UHFFFAOYSA-N 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- XXTMOOYXURHAHD-UHFFFAOYSA-N diazanium 3-carboxy-3,5-dihydroxy-5-oxopentanoate chloride Chemical compound C(CC(O)(C(=O)O)CC(=O)O)(=O)[O-].[NH4+].[Cl-].[NH4+] XXTMOOYXURHAHD-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/10—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2254701A DE2254701C3 (de) | 1972-11-09 | 1972-11-09 | Verfahren zur Herstellung von in 2- und 5-Stellung substituierten Thiazolinen-(3) |
| ES418694A ES418694A1 (es) | 1972-11-09 | 1973-09-12 | Procedimiento para la preparacion de tiazolinas-(3) susti- tuidas en posiciones 2 y 5. |
| DD173588A DD107464A5 (OSRAM) | 1972-11-09 | 1973-09-20 | |
| CH1373073A CH592643A5 (OSRAM) | 1972-11-09 | 1973-09-25 | |
| CA182,070A CA1005448A (en) | 1972-11-09 | 1973-09-27 | Process for producing thiazolines -(3) |
| GB4995373A GB1435332A (en) | 1972-11-09 | 1973-10-26 | Process for the production of 3-thiazolines |
| FR7338492A FR2206322B1 (OSRAM) | 1972-11-09 | 1973-10-29 | |
| US05/413,048 US3931208A (en) | 1972-11-09 | 1973-11-05 | Process for the production of thiazolines-(3) |
| IT53550/73A IT1000138B (it) | 1972-11-09 | 1973-11-07 | Procedimento per la produzione di tiazoline 3 |
| AT939673A AT327888B (de) | 1972-11-09 | 1973-11-08 | Verfahren zur herstellung von in 2- und 5-stellung substituierten thiazolinen-(3) |
| BE6044354A BE807087A (fr) | 1972-11-09 | 1973-11-08 | Procede pour la preparation de thiazolines-(3) |
| JP12613173A JPS5315063B2 (OSRAM) | 1972-11-09 | 1973-11-09 | |
| NL7315388.A NL159664B (nl) | 1972-11-09 | 1973-11-09 | Werkwijze ter bereiding van op de 2- en 5-plaats gesubsti- tueerde thiazolinen-(3). |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2254701A DE2254701C3 (de) | 1972-11-09 | 1972-11-09 | Verfahren zur Herstellung von in 2- und 5-Stellung substituierten Thiazolinen-(3) |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2254701A1 DE2254701A1 (de) | 1974-05-16 |
| DE2254701B2 DE2254701B2 (de) | 1978-03-09 |
| DE2254701C3 true DE2254701C3 (de) | 1978-12-07 |
Family
ID=5861153
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2254701A Expired DE2254701C3 (de) | 1972-11-09 | 1972-11-09 | Verfahren zur Herstellung von in 2- und 5-Stellung substituierten Thiazolinen-(3) |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3931208A (OSRAM) |
| JP (1) | JPS5315063B2 (OSRAM) |
| AT (1) | AT327888B (OSRAM) |
| BE (1) | BE807087A (OSRAM) |
| CA (1) | CA1005448A (OSRAM) |
| CH (1) | CH592643A5 (OSRAM) |
| DD (1) | DD107464A5 (OSRAM) |
| DE (1) | DE2254701C3 (OSRAM) |
| ES (1) | ES418694A1 (OSRAM) |
| FR (1) | FR2206322B1 (OSRAM) |
| GB (1) | GB1435332A (OSRAM) |
| IT (1) | IT1000138B (OSRAM) |
| NL (1) | NL159664B (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4415738A (en) | 1980-07-11 | 1983-11-15 | Degussa Aktiengesellschaft | Process for the production thiazolines-(3) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4066657A (en) * | 1976-04-26 | 1978-01-03 | Pfizer Inc. | 2-[(Carboxy)(triphenylmethylamino)methyl]-5,5-dimethyl-3-thiazoline |
| US4040987A (en) * | 1976-10-07 | 1977-08-09 | International Flavors & Fragrances Inc. | 2-Alkyl-substituted-4,5-dimethyl thiazoline perfume and cologne compositions |
| DE2645731C2 (de) * | 1976-10-09 | 1986-05-07 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Thiazolinen-(3) |
| FR3153833B1 (fr) | 2023-10-10 | 2025-10-03 | Snf Sa | Procédé de fabrication d’une feuille de papier |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE547299A (OSRAM) * | 1955-11-30 | |||
| US3004981A (en) * | 1957-08-09 | 1961-10-17 | Leuna Werke Veb | Process for the preparation of delta-3, 4-thiazolines |
| CH529162A (de) * | 1968-09-06 | 1972-10-15 | Degussa | Verfahren zur Herstellung von Thiazolinen- 3 |
-
1972
- 1972-11-09 DE DE2254701A patent/DE2254701C3/de not_active Expired
-
1973
- 1973-09-12 ES ES418694A patent/ES418694A1/es not_active Expired
- 1973-09-20 DD DD173588A patent/DD107464A5/xx unknown
- 1973-09-25 CH CH1373073A patent/CH592643A5/xx not_active IP Right Cessation
- 1973-09-27 CA CA182,070A patent/CA1005448A/en not_active Expired
- 1973-10-26 GB GB4995373A patent/GB1435332A/en not_active Expired
- 1973-10-29 FR FR7338492A patent/FR2206322B1/fr not_active Expired
- 1973-11-05 US US05/413,048 patent/US3931208A/en not_active Expired - Lifetime
- 1973-11-07 IT IT53550/73A patent/IT1000138B/it active
- 1973-11-08 BE BE6044354A patent/BE807087A/xx not_active IP Right Cessation
- 1973-11-08 AT AT939673A patent/AT327888B/de not_active IP Right Cessation
- 1973-11-09 JP JP12613173A patent/JPS5315063B2/ja not_active Expired
- 1973-11-09 NL NL7315388.A patent/NL159664B/xx not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4415738A (en) | 1980-07-11 | 1983-11-15 | Degussa Aktiengesellschaft | Process for the production thiazolines-(3) |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2206322B1 (OSRAM) | 1978-11-17 |
| NL7315388A (OSRAM) | 1974-05-13 |
| IT1000138B (it) | 1976-03-30 |
| BE807087A (fr) | 1974-05-08 |
| DE2254701A1 (de) | 1974-05-16 |
| AT327888B (de) | 1976-02-25 |
| CH592643A5 (OSRAM) | 1977-10-31 |
| GB1435332A (en) | 1976-05-12 |
| JPS5315063B2 (OSRAM) | 1978-05-22 |
| JPS49133373A (OSRAM) | 1974-12-21 |
| ES418694A1 (es) | 1976-02-16 |
| FR2206322A1 (OSRAM) | 1974-06-07 |
| NL159664B (nl) | 1979-03-15 |
| ATA939673A (de) | 1975-05-15 |
| DD107464A5 (OSRAM) | 1974-08-05 |
| US3931208A (en) | 1976-01-06 |
| CA1005448A (en) | 1977-02-15 |
| DE2254701B2 (de) | 1978-03-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |