BE561347A - - Google Patents
Info
- Publication number
- BE561347A BE561347A BE561347DA BE561347A BE 561347 A BE561347 A BE 561347A BE 561347D A BE561347D A BE 561347DA BE 561347 A BE561347 A BE 561347A
- Authority
- BE
- Belgium
- Prior art keywords
- general formula
- phenyl
- parts
- radical
- appended
- Prior art date
Links
- 230000000875 corresponding Effects 0.000 claims description 30
- -1 alkali metal iodate Chemical class 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000011780 sodium chloride Substances 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 9
- YCIMNLLNPGFGHC-UHFFFAOYSA-N Catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 8
- 150000004982 aromatic amines Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000007859 condensation product Substances 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N O-Phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-Chloroaniline Chemical class NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-Benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- WTCBONOLBHEDIL-UHFFFAOYSA-M Sodium iodate Chemical compound [Na+].[O-]I(=O)=O WTCBONOLBHEDIL-UHFFFAOYSA-M 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 230000001590 oxidative Effects 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000011697 sodium iodate Substances 0.000 description 4
- 229940032753 sodium iodate Drugs 0.000 description 4
- 235000015281 sodium iodate Nutrition 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- BHAAPTBBJKJZER-UHFFFAOYSA-N P-Anisidine Chemical class COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical compound C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 125000004467 aryl imino group Chemical group 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 150000002988 phenazines Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000001549 tubercolostatic Effects 0.000 description 3
- WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-Benzoquinone Chemical compound O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 description 2
- QDAKPTLLVBBHMP-UHFFFAOYSA-N 2-N-phenylbenzene-1,2-diamine;hydrochloride Chemical compound Cl.NC1=CC=CC=C1NC1=CC=CC=C1 QDAKPTLLVBBHMP-UHFFFAOYSA-N 0.000 description 2
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-Bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 2
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 241001024304 Mino Species 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N Silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 150000004994 m-toluidines Chemical class 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 150000004995 p-toluidines Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000814 tuberculostatic agent Substances 0.000 description 2
- CAFAOQIVXSSFSY-UHFFFAOYSA-N 1-ethoxyethanol Chemical compound CCOC(C)O CAFAOQIVXSSFSY-UHFFFAOYSA-N 0.000 description 1
- GMOGVMIKHQEKMP-UHFFFAOYSA-N 2,10-dihydrophenazine Chemical compound C1=CC=C2NC3=CCC=CC3=NC2=C1 GMOGVMIKHQEKMP-UHFFFAOYSA-N 0.000 description 1
- BAHZMOXWABTQEM-UHFFFAOYSA-N 2-N-(4-propan-2-yloxyphenyl)benzene-1,2-diamine Chemical compound C1=CC(OC(C)C)=CC=C1NC1=CC=CC=C1N BAHZMOXWABTQEM-UHFFFAOYSA-N 0.000 description 1
- YQACKMXMLJSWFM-UHFFFAOYSA-N 2-N-cyclohexylbenzene-1,2-diamine Chemical compound NC1=CC=CC=C1NC1CCCCC1 YQACKMXMLJSWFM-UHFFFAOYSA-N 0.000 description 1
- NFCPRRWCTNLGSN-UHFFFAOYSA-N 2-N-phenylbenzene-1,2-diamine Chemical compound NC1=CC=CC=C1NC1=CC=CC=C1 NFCPRRWCTNLGSN-UHFFFAOYSA-N 0.000 description 1
- HRXZRAXKKNUKRF-UHFFFAOYSA-N 4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1 HRXZRAXKKNUKRF-UHFFFAOYSA-N 0.000 description 1
- DJRKHTCUXRGYEU-UHFFFAOYSA-N 4-hexoxyaniline Chemical compound CCCCCCOC1=CC=C(N)C=C1 DJRKHTCUXRGYEU-UHFFFAOYSA-N 0.000 description 1
- MLNFMFAMNBGAQT-UHFFFAOYSA-N 4-propan-2-yloxyaniline Chemical compound CC(C)OC1=CC=C(N)C=C1 MLNFMFAMNBGAQT-UHFFFAOYSA-N 0.000 description 1
- DWOIGSLSPPLRKO-UHFFFAOYSA-N 4-propoxyaniline Chemical compound CCCOC1=CC=C(N)C=C1 DWOIGSLSPPLRKO-UHFFFAOYSA-N 0.000 description 1
- YQYVCESNZUNSHJ-UHFFFAOYSA-N Cl.Cl.Cl.C(C)N(CC)CCNC1=C(C=CC=C1)N Chemical compound Cl.Cl.Cl.C(C)N(CC)CCNC1=C(C=CC=C1)N YQYVCESNZUNSHJ-UHFFFAOYSA-N 0.000 description 1
- 241001182492 Nes Species 0.000 description 1
- 241000577218 Phenes Species 0.000 description 1
- 240000004760 Pimpinella anisum Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 244000052616 bacterial pathogens Species 0.000 description 1
- JNIGYQOBELCEIZ-MAKDUZDQSA-L barium(2+);5-chloro-4-methyl-2-[(2Z)-2-(2-oxonaphthalen-1-ylidene)hydrazinyl]benzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N\N=C/2C3=CC=CC=C3C=CC\2=O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N\N=C/2C3=CC=CC=C3C=CC\2=O)=C1S([O-])(=O)=O JNIGYQOBELCEIZ-MAKDUZDQSA-L 0.000 description 1
- WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000973 chemotherapeutic Effects 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000001145 hydrido group Chemical group *[H] 0.000 description 1
- DKEONVNYXODZRQ-UHFFFAOYSA-N hydron;2-N-methylbenzene-1,2-diamine;dichloride Chemical compound Cl.Cl.CNC1=CC=CC=C1N DKEONVNYXODZRQ-UHFFFAOYSA-N 0.000 description 1
- 125000000879 imine group Chemical group 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical class [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004987 o-phenylenediamines Chemical class 0.000 description 1
- 150000004993 o-toluidines Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/46—Phenazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE561347A true BE561347A (es) |
Family
ID=183326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE561347D BE561347A (es) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE561347A (es) |
-
0
- BE BE561347D patent/BE561347A/fr unknown
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