DE2107348A1 - Verfahren zur Herstellung von 5-(l,3-Diazacycloalk-2-enyl)-oxdiazolen-0,3,4) - Google Patents
Verfahren zur Herstellung von 5-(l,3-Diazacycloalk-2-enyl)-oxdiazolen-0,3,4)Info
- Publication number
- DE2107348A1 DE2107348A1 DE19712107348 DE2107348A DE2107348A1 DE 2107348 A1 DE2107348 A1 DE 2107348A1 DE 19712107348 DE19712107348 DE 19712107348 DE 2107348 A DE2107348 A DE 2107348A DE 2107348 A1 DE2107348 A1 DE 2107348A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- parts
- enyl
- oxdiazole
- radicals
- 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 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- -1 o-chlorophenyl- Chemical group 0.000 description 15
- 229910052717 sulfur Inorganic materials 0.000 description 13
- 239000011593 sulfur Substances 0.000 description 13
- 239000007858 starting material Substances 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 8
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 3
- SRGQQZYVZFJYHJ-UHFFFAOYSA-N 2-(aminomethyl)cyclopentan-1-amine Chemical compound NCC1CCCC1N SRGQQZYVZFJYHJ-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- MYJQGGALXPHWLV-UHFFFAOYSA-N cyclopentane-1,2-diamine Chemical compound NC1CCCC1N MYJQGGALXPHWLV-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZUYYQGFCSKJGDO-UHFFFAOYSA-N 2-(aminomethyl)cyclohexan-1-amine Chemical compound NCC1CCCCC1N ZUYYQGFCSKJGDO-UHFFFAOYSA-N 0.000 description 1
- DIKQYXQNRSMPGZ-UHFFFAOYSA-N 2-ethylhexane-1,3-diamine Chemical compound CCCC(N)C(CC)CN DIKQYXQNRSMPGZ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- LAQJMLVXOJSWOI-UHFFFAOYSA-N N[ClH]N Chemical compound N[ClH]N LAQJMLVXOJSWOI-UHFFFAOYSA-N 0.000 description 1
- 241000092161 Pithys Species 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 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
- RGTXVXDNHPWPHH-UHFFFAOYSA-N butane-1,3-diamine Chemical compound CC(N)CCN RGTXVXDNHPWPHH-UHFFFAOYSA-N 0.000 description 1
- GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical compound CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- IWCAQTQMDRGMPI-UHFFFAOYSA-N hexane-3,4-diamine Chemical compound CCC(N)C(N)CC IWCAQTQMDRGMPI-UHFFFAOYSA-N 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712107348 DE2107348A1 (de) | 1971-02-16 | 1971-02-16 | Verfahren zur Herstellung von 5-(l,3-Diazacycloalk-2-enyl)-oxdiazolen-0,3,4) |
| CH102472A CH574957A5 (enExample) | 1971-02-16 | 1972-01-24 | |
| BE779320A BE779320A (fr) | 1971-02-16 | 1972-02-14 | Procede de preparation de 2-(1,3-diaza-2-cycloalcenyl)-1,3, 4-oxadiazoles |
| FR7204846A FR2125897A5 (en) | 1971-02-16 | 1972-02-14 | 5-(1,3-diazacycloalk-2-enyl)-1,3,4-oxadiazoles - useful as textile assistants, plant-protection agents and intermediates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712107348 DE2107348A1 (de) | 1971-02-16 | 1971-02-16 | Verfahren zur Herstellung von 5-(l,3-Diazacycloalk-2-enyl)-oxdiazolen-0,3,4) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2107348A1 true DE2107348A1 (de) | 1972-08-31 |
Family
ID=5798930
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712107348 Pending DE2107348A1 (de) | 1971-02-16 | 1971-02-16 | Verfahren zur Herstellung von 5-(l,3-Diazacycloalk-2-enyl)-oxdiazolen-0,3,4) |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE779320A (enExample) |
| CH (1) | CH574957A5 (enExample) |
| DE (1) | DE2107348A1 (enExample) |
| FR (1) | FR2125897A5 (enExample) |
-
1971
- 1971-02-16 DE DE19712107348 patent/DE2107348A1/de active Pending
-
1972
- 1972-01-24 CH CH102472A patent/CH574957A5/xx not_active IP Right Cessation
- 1972-02-14 BE BE779320A patent/BE779320A/xx not_active IP Right Cessation
- 1972-02-14 FR FR7204846A patent/FR2125897A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH574957A5 (enExample) | 1976-04-30 |
| FR2125897A5 (en) | 1972-09-29 |
| BE779320A (fr) | 1972-08-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OHN | Withdrawal |