BE501176A - - Google Patents

Info

Publication number

BE501176A

BE501176A BE501176DA BE501176A BE 501176 A BE501176 A BE 501176A BE 501176D A BE501176D A BE 501176DA BE 501176 A BE501176 A BE 501176A

Authority

BE

Belgium

Prior art keywords

product

phenyl

hydroboride

nitro

condensation

Prior art date

Links

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• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 16
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
• XHODMTAOVMFHQJ-UHFFFAOYSA-N aluminum;propan-2-ol Chemical compound [Al].CC(C)O XHODMTAOVMFHQJ-UHFFFAOYSA-N 0.000 claims description 4
• 238000009833 condensation Methods 0.000 claims description 4
• 230000005494 condensation Effects 0.000 claims description 4
• 238000000034 method Methods 0.000 claims description 3
• 239000003638 reducing agent Substances 0.000 claims description 3
• 239000003513 alkali Substances 0.000 claims description 2
• 229910052782 aluminium Inorganic materials 0.000 claims description 2
• -1 aluminum alkoxide Chemical class 0.000 claims description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
• 229910052700 potassium Inorganic materials 0.000 claims description 2
• 239000011591 potassium Substances 0.000 claims description 2
• KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
• 229910052708 sodium Inorganic materials 0.000 claims description 2
• 239000011734 sodium Substances 0.000 claims description 2
• 239000002904 solvent Substances 0.000 claims description 2
• QEKPBYCXURULNE-UHFFFAOYSA-N 2-aminopropane-1,1-diol Chemical compound CC(N)C(O)O QEKPBYCXURULNE-UHFFFAOYSA-N 0.000 claims 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
• 239000000047 product Substances 0.000 description 11
• 239000000243 solution Substances 0.000 description 11
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
• KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
• ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 239000007859 condensation product Substances 0.000 description 5
• 210000001736 Capillaries Anatomy 0.000 description 4
• 239000000203 mixture Substances 0.000 description 4
• YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
• LMRDBJZQDUVCQH-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)acetaldehyde Chemical compound C1=CC=C2C(=O)N(CC=O)C(=O)C2=C1 LMRDBJZQDUVCQH-UHFFFAOYSA-N 0.000 description 3
• 239000003795 chemical substances by application Substances 0.000 description 3
• 238000001816 cooling Methods 0.000 description 3
• 238000002844 melting Methods 0.000 description 3
• 239000002244 precipitate Substances 0.000 description 3
• 239000000725 suspension Substances 0.000 description 3
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
• IQFVPQOLBLOTPF-HKXUKFGYSA-L Congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• 125000003158 alcohol group Chemical group 0.000 description 2
• 150000001299 aldehydes Chemical group 0.000 description 2
• 150000001875 compounds Chemical class 0.000 description 2
• 238000001704 evaporation Methods 0.000 description 2
• 238000000605 extraction Methods 0.000 description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
• 238000002360 preparation method Methods 0.000 description 2
• CMWKITSNTDAEDT-UHFFFAOYSA-N 2-Nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 1
• KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 1
• VRDBIJCCXDEZJN-UHFFFAOYSA-M 2-piperidin-1-ylacetate Chemical compound [O-]C(=O)CN1CCCCC1 VRDBIJCCXDEZJN-UHFFFAOYSA-M 0.000 description 1
• BXRFQSNOROATLV-UHFFFAOYSA-N 4-Nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
• OFCNXPDARWKPPY-UHFFFAOYSA-N Allopurinol Chemical compound OC1=NC=NC2=C1C=NN2 OFCNXPDARWKPPY-UHFFFAOYSA-N 0.000 description 1
• 229940064005 Antibiotic throat preparations Drugs 0.000 description 1
• 229940083879 Antibiotics FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE Drugs 0.000 description 1
• 229940042052 Antibiotics for systemic use Drugs 0.000 description 1
• 229940042786 Antitubercular Antibiotics Drugs 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• WIIZWVCIJKGZOK-RKDXNWHRSA-N Chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
• FXHOOIRPVKKKFG-UHFFFAOYSA-N DMA Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
• ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 1
• 229940093922 Gynecological Antibiotics Drugs 0.000 description 1
• NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
• 229940024982 Topical Antifungal Antibiotics Drugs 0.000 description 1
• 239000002253 acid Substances 0.000 description 1
• 238000007792 addition Methods 0.000 description 1
• 238000006668 aldol addition reaction Methods 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 239000003242 anti bacterial agent Substances 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 230000003115 biocidal Effects 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 239000012043 crude product Substances 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• 230000003301 hydrolyzing Effects 0.000 description 1
• 229940079866 intestinal antibiotics Drugs 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
• 229910052753 mercury Inorganic materials 0.000 description 1
• 229940005935 ophthalmologic Antibiotics Drugs 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 230000020477 pH reduction Effects 0.000 description 1
• 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
• NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
• 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• 230000002194 synthesizing Effects 0.000 description 1
• 238000005406 washing Methods 0.000 description 1

Cited By (1)