DE2131927A1 - Neue 2-Nitro-benzofurane und Verfahren zu deren Herstellung - Google Patents
Neue 2-Nitro-benzofurane und Verfahren zu deren HerstellungInfo
- Publication number
- DE2131927A1 DE2131927A1 DE19712131927 DE2131927A DE2131927A1 DE 2131927 A1 DE2131927 A1 DE 2131927A1 DE 19712131927 DE19712131927 DE 19712131927 DE 2131927 A DE2131927 A DE 2131927A DE 2131927 A1 DE2131927 A1 DE 2131927A1
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- compound
- methyl
- hydrogen
- benzofuran
- 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 14
- RSZMTXPFGDUHSE-UHFFFAOYSA-N 2-nitro-1-benzofuran Chemical class C1=CC=C2OC([N+](=O)[O-])=CC2=C1 RSZMTXPFGDUHSE-UHFFFAOYSA-N 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 20
- DNPRVXJGNANVCZ-UHFFFAOYSA-N bromo(nitro)methane Chemical compound [O-][N+](=O)CBr DNPRVXJGNANVCZ-UHFFFAOYSA-N 0.000 claims description 14
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 14
- 150000001299 aldehydes Chemical class 0.000 claims description 8
- -1 2-nitro-6-chloro-benzofuran Chemical compound 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000002609 medium Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 241000894006 Bacteria Species 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 235000015097 nutrients Nutrition 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 5
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 5
- 241000224527 Trichomonas vaginalis Species 0.000 description 5
- AZXFRACMLPEVGC-UHFFFAOYSA-N 7-methoxy-2-nitro-1-benzofuran Chemical compound COC1=CC=CC2=C1OC([N+]([O-])=O)=C2 AZXFRACMLPEVGC-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LHKZBAAZHMQJBL-UHFFFAOYSA-N 5-chloro-2-nitro-1-benzofuran Chemical compound ClC1=CC=C2OC([N+](=O)[O-])=CC2=C1 LHKZBAAZHMQJBL-UHFFFAOYSA-N 0.000 description 3
- 241000228212 Aspergillus Species 0.000 description 3
- 241000304886 Bacilli Species 0.000 description 3
- 241000224431 Entamoeba Species 0.000 description 3
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000002054 inoculum Substances 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 201000008827 tuberculosis Diseases 0.000 description 3
- WZUODJNEIXSNEU-UHFFFAOYSA-N 2-Hydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(O)=C1 WZUODJNEIXSNEU-UHFFFAOYSA-N 0.000 description 2
- MQJDCMRJYZIXBB-UHFFFAOYSA-N 5-methoxy-2-nitro-1-benzofuran Chemical compound COC1=CC=C2OC([N+]([O-])=O)=CC2=C1 MQJDCMRJYZIXBB-UHFFFAOYSA-N 0.000 description 2
- FZHSPPYCNDYIKD-UHFFFAOYSA-N 5-methoxysalicylaldehyde Chemical compound COC1=CC=C(O)C(C=O)=C1 FZHSPPYCNDYIKD-UHFFFAOYSA-N 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- 244000026610 Cynodon dactylon var. affinis Species 0.000 description 2
- 239000006159 Sabouraud's agar Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241000295644 Staphylococcaceae Species 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000013081 microcrystal Substances 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000012449 sabouraud dextrose agar Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- ILEIUTCVWLYZOM-UHFFFAOYSA-N 2-hydroxy-5-methylbenzaldehyde Chemical compound CC1=CC=C(O)C(C=O)=C1 ILEIUTCVWLYZOM-UHFFFAOYSA-N 0.000 description 1
- QNZWAJZEJAOVPN-UHFFFAOYSA-N 4-chloro-2-hydroxybenzaldehyde Chemical compound OC1=CC(Cl)=CC=C1C=O QNZWAJZEJAOVPN-UHFFFAOYSA-N 0.000 description 1
- QEXAZOMOZUCOGO-UHFFFAOYSA-N 5-bromo-2-hydroxy-4-methylbenzaldehyde Chemical compound CC1=CC(O)=C(C=O)C=C1Br QEXAZOMOZUCOGO-UHFFFAOYSA-N 0.000 description 1
- MKKSTJKBKNCMRV-UHFFFAOYSA-N 5-bromo-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(Br)C=C1C=O MKKSTJKBKNCMRV-UHFFFAOYSA-N 0.000 description 1
- DGDCGRHRZISVAR-UHFFFAOYSA-N 5-bromo-2-nitro-1-benzofuran Chemical compound BrC1=CC=C2OC([N+](=O)[O-])=CC2=C1 DGDCGRHRZISVAR-UHFFFAOYSA-N 0.000 description 1
- TVDVRKLTHSTZTH-UHFFFAOYSA-N 5-chloro-2-hydroxy-4-methylbenzaldehyde Chemical compound CC1=CC(O)=C(C=O)C=C1Cl TVDVRKLTHSTZTH-UHFFFAOYSA-N 0.000 description 1
- FUGKCSRLAQKUHG-UHFFFAOYSA-N 5-chloro-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(Cl)C=C1C=O FUGKCSRLAQKUHG-UHFFFAOYSA-N 0.000 description 1
- GDXGCYKZSGUDLX-UHFFFAOYSA-N 6-methoxy-2-nitro-1-benzofuran Chemical compound COC1=CC=C2C=C([N+]([O-])=O)OC2=C1 GDXGCYKZSGUDLX-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 208000004881 Amebiasis Diseases 0.000 description 1
- 206010001980 Amoebiasis Diseases 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000224526 Trichomonas Species 0.000 description 1
- 208000032159 Vaginal inflammation Diseases 0.000 description 1
- 201000008100 Vaginitis Diseases 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 230000003569 amebicidal effect Effects 0.000 description 1
- 230000001857 anti-mycotic effect Effects 0.000 description 1
- 239000002543 antimycotic Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 235000021336 beef liver Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 210000005027 intestinal barrier Anatomy 0.000 description 1
- 230000007358 intestinal barrier function Effects 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000006402 liver broth Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 239000002297 parasiticide Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 206010051250 ureteritis Diseases 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7023984A FR2092891A1 (en) | 1970-06-29 | 1970-06-29 | 2-nitro-benzofuran derivs - antimicrobial, antiparasitic - cpd prepd from salicylaldehyde and halo-nitro methane |
| FR7109707A FR2129894A2 (en) | 1971-03-19 | 1971-03-19 | 2-nitro-benzofuran derivs - antimicrobial, antiparasitic - cpd prepd from salicylaldehyde and halo-nitro methane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2131927A1 true DE2131927A1 (de) | 1972-02-03 |
Family
ID=26215826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712131927 Pending DE2131927A1 (de) | 1970-06-29 | 1971-06-26 | Neue 2-Nitro-benzofurane und Verfahren zu deren Herstellung |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3838173A (enExample) |
| JP (1) | JPS5542992B1 (enExample) |
| AT (1) | AT306711B (enExample) |
| BE (1) | BE768603A (enExample) |
| CA (1) | CA963474A (enExample) |
| CH (1) | CH524596A (enExample) |
| DE (1) | DE2131927A1 (enExample) |
| GB (1) | GB1332713A (enExample) |
| NL (1) | NL7108906A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1068110B (it) * | 1976-08-13 | 1985-03-21 | Montedison Spa | Processo per la preparazione di aldeidi 2 idrossibenzoiche |
| CN113185493B (zh) * | 2021-04-21 | 2023-06-20 | 西北农林科技大学 | 水杨醛类化合物、制备方法及其防治猕猴桃溃疡病的应用 |
-
1971
- 1971-06-16 BE BE768603A patent/BE768603A/xx unknown
- 1971-06-22 CA CA116,267*7A patent/CA963474A/en not_active Expired
- 1971-06-24 CH CH928571A patent/CH524596A/fr not_active IP Right Cessation
- 1971-06-26 DE DE19712131927 patent/DE2131927A1/de active Pending
- 1971-06-28 US US00157643A patent/US3838173A/en not_active Expired - Lifetime
- 1971-06-28 NL NL7108906A patent/NL7108906A/xx not_active Application Discontinuation
- 1971-06-28 GB GB3027871A patent/GB1332713A/en not_active Expired
- 1971-06-29 JP JP4692271A patent/JPS5542992B1/ja active Pending
- 1971-06-29 AT AT564571A patent/AT306711B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7108906A (enExample) | 1971-12-31 |
| AT306711B (de) | 1973-04-25 |
| CH524596A (fr) | 1972-06-30 |
| US3838173A (en) | 1974-09-24 |
| JPS5542992B1 (enExample) | 1980-11-04 |
| CA963474A (en) | 1975-02-25 |
| GB1332713A (en) | 1973-10-03 |
| BE768603A (fr) | 1971-11-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OHN | Withdrawal |