BE503980A - - Google Patents
Info
- Publication number
- BE503980A BE503980A BE503980DA BE503980A BE 503980 A BE503980 A BE 503980A BE 503980D A BE503980D A BE 503980DA BE 503980 A BE503980 A BE 503980A
- Authority
- BE
- Belgium
- Prior art keywords
- triazine
- derivatives
- thiosemicarbazide
- mercapto
- aldehyde
- Prior art date
Links
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 claims description 16
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 150000001299 aldehydes Chemical group 0.000 claims description 10
- 150000002576 ketones Chemical class 0.000 claims description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- 150000003583 thiosemicarbazides Chemical class 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 150000003568 thioethers Chemical class 0.000 claims description 8
- 235000005074 zinc chloride Nutrition 0.000 claims description 8
- 239000011592 zinc chloride Substances 0.000 claims description 8
- SOFPIAMTOZWXKT-UHFFFAOYSA-N 2h-1,2,4-triazine-3-thione Chemical class SC1=NC=CN=N1 SOFPIAMTOZWXKT-UHFFFAOYSA-N 0.000 claims description 7
- JDXKTOBMLZLCSB-UHFFFAOYSA-N anilinothiourea Chemical class NC(=S)NNC1=CC=CC=C1 JDXKTOBMLZLCSB-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 claims description 7
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 7
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 5
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229940015043 glyoxal Drugs 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 claims description 3
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 claims description 3
- LONQTZORWVBHMK-UHFFFAOYSA-N [N].NN Chemical group [N].NN LONQTZORWVBHMK-UHFFFAOYSA-N 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001348 alkyl chlorides Chemical class 0.000 claims description 2
- WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical compound O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 claims 1
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- 150000001728 carbonyl compounds Chemical class 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
- 235000019441 ethanol Nutrition 0.000 description 25
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- 239000000843 powder Substances 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 229940117916 cinnamic aldehyde Drugs 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 10
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 8
- 235000011118 potassium hydroxide Nutrition 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 240000007817 Olea europaea Species 0.000 description 6
- AXMVYSVVTMKQSL-UHFFFAOYSA-N UNPD142122 Natural products OC1=CC=C(C=CC=O)C=C1O AXMVYSVVTMKQSL-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 150000003584 thiosemicarbazones Chemical class 0.000 description 5
- 150000005840 aryl radicals Chemical class 0.000 description 4
- 230000004927 fusion Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- -1 p-methoxy -benzylidene Chemical group 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- SRXWGYPOOZFWAD-UHFFFAOYSA-N 4-(3-phenylprop-2-enoxy)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1OCC=CC1=CC=CC=C1 SRXWGYPOOZFWAD-UHFFFAOYSA-N 0.000 description 2
- ZVTWZSXLLMNMQC-UHFFFAOYSA-N 4-phenylmethoxybenzaldehyde Chemical compound C1=CC(C=O)=CC=C1OCC1=CC=CC=C1 ZVTWZSXLLMNMQC-UHFFFAOYSA-N 0.000 description 2
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 150000007659 semicarbazones Chemical class 0.000 description 2
- MPHXZUBEUTVHNH-UHFFFAOYSA-N 5-methyl-2h-1,2,4-triazine-3-thione Chemical compound CC1=CN=NC(S)=N1 MPHXZUBEUTVHNH-UHFFFAOYSA-N 0.000 description 1
- VAJIWQOICFDLIH-UHFFFAOYSA-N C(C)(=O)O.N1=NC=NC=C1 Chemical compound C(C)(=O)O.N1=NC=NC=C1 VAJIWQOICFDLIH-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 230000001364 causal effect Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 229940043350 citral Drugs 0.000 description 1
- WTEVQBCEXWBHNA-YFHOEESVSA-N citral B Natural products CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 239000002297 parasiticide Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
Landscapes
- Cosmetics (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE503980A true BE503980A (enrdf_load_html_response) |
Family
ID=144978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE503980D BE503980A (enrdf_load_html_response) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE503980A (enrdf_load_html_response) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012140254A1 (fr) | 2011-04-14 | 2012-10-18 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant un dérivé de la thiazoline |
| WO2012140258A2 (fr) | 2011-04-14 | 2012-10-18 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant un dérivé de thiazole |
| WO2012140251A1 (fr) | 2011-04-14 | 2012-10-18 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant un derive du thiadiazole |
| WO2012140259A1 (fr) | 2011-04-14 | 2012-10-18 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant un dérivé du thiophène |
| WO2012140255A2 (fr) | 2011-04-14 | 2012-10-18 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant un dérivé de la 1,2,4-triazine |
-
0
- BE BE503980D patent/BE503980A/fr unknown
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012140254A1 (fr) | 2011-04-14 | 2012-10-18 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant un dérivé de la thiazoline |
| WO2012140258A2 (fr) | 2011-04-14 | 2012-10-18 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant un dérivé de thiazole |
| WO2012140251A1 (fr) | 2011-04-14 | 2012-10-18 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant un derive du thiadiazole |
| WO2012140259A1 (fr) | 2011-04-14 | 2012-10-18 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant un dérivé du thiophène |
| WO2012140255A2 (fr) | 2011-04-14 | 2012-10-18 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant un dérivé de la 1,2,4-triazine |
| US9040618B2 (en) | 2011-04-14 | 2015-05-26 | Compagnie Generale Des Etablissements Michelin | Rubber composition including a 1,2,4-triazine derivative |
| US9550891B2 (en) | 2011-04-14 | 2017-01-24 | Compagnie Generale Des Etablissements Michelin | Rubber composition comprising a thiazoline derivative |
| US9688852B2 (en) | 2011-04-14 | 2017-06-27 | Compagnie Generale Des Etablissements Michelin | Rubber composition including a thiazole derivative |