CH513130A - Verfahren zur Herstellung von neuen N-Naphthyl- bzw. N-Tetrahydronaphthylformiminoäthern - Google Patents
Verfahren zur Herstellung von neuen N-Naphthyl- bzw. N-TetrahydronaphthylformiminoäthernInfo
- Publication number
- CH513130A CH513130A CH562467A CH562467A CH513130A CH 513130 A CH513130 A CH 513130A CH 562467 A CH562467 A CH 562467A CH 562467 A CH562467 A CH 562467A CH 513130 A CH513130 A CH 513130A
- Authority
- CH
- Switzerland
- Prior art keywords
- naphthyl
- formimino
- formula
- mol
- ether
- Prior art date
Links
- 230000000507 anthelmentic effect Effects 0.000 title abstract description 4
- 229940124339 anthelmintic agent Drugs 0.000 title abstract description 3
- 239000000921 anthelmintic agent Substances 0.000 title abstract description 3
- 150000002170 ethers Chemical class 0.000 title description 4
- -1 N-tetrahydro naphthyl-formimino ethers Chemical class 0.000 claims abstract description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 16
- 229940035423 ethyl ether Drugs 0.000 claims description 16
- 230000001419 dependent effect Effects 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 4
- 239000000155 melt Substances 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 229960000541 cetyl alcohol Drugs 0.000 claims description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 2
- 229940067107 phenylethyl alcohol Drugs 0.000 claims description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 2
- 238000005690 transetherification reaction Methods 0.000 claims 3
- 239000012454 non-polar solvent Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 abstract description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 11
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 4
- IHHYWKHAIABDMI-UHFFFAOYSA-N C1(CCCC2=CC=CC=C12)N=COC=NC1CCCC2=CC=CC=C12 Chemical class C1(CCCC2=CC=CC=C12)N=COC=NC1CCCC2=CC=CC=C12 IHHYWKHAIABDMI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 4
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DRRNJGZQVQYOKA-UHFFFAOYSA-N 3-hydroxy-4-[1-[2-(2-hydroxy-4-sulfonaphthalen-1-yl)-3-iminopropoxy]-3-iminopropan-2-yl]naphthalene-1-sulfonic acid Chemical compound OC1=C(C2=CC=CC=C2C(=C1)S(=O)(=O)O)C(COCC(C1=C(C=C(C2=CC=CC=C12)S(=O)(=O)O)O)C=N)C=N DRRNJGZQVQYOKA-UHFFFAOYSA-N 0.000 description 1
- RXCMFQDTWCCLBL-UHFFFAOYSA-N 4-amino-3-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 RXCMFQDTWCCLBL-UHFFFAOYSA-N 0.000 description 1
- UDKKZFWHYQYRLF-UHFFFAOYSA-N C1(CCCC2=CC=CC=C12)N=CCOCC=NC1CCCC2=CC=CC=C12 Chemical compound C1(CCCC2=CC=CC=C12)N=CCOCC=NC1CCCC2=CC=CC=C12 UDKKZFWHYQYRLF-UHFFFAOYSA-N 0.000 description 1
- 241000243676 Enchytraeus albidus Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 208000002474 Tinea Diseases 0.000 description 1
- 241000893966 Trichophyton verrucosum Species 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- OJYGBLRPYBAHRT-UHFFFAOYSA-N alphachloralose Chemical compound O1C(C(Cl)(Cl)Cl)OC2C(O)C(C(O)CO)OC21 OJYGBLRPYBAHRT-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000002463 imidates Chemical class 0.000 description 1
- UKOVZLWSUZKTRL-UHFFFAOYSA-N naphthalid Chemical compound C1=CC(C(=O)OC2)=C3C2=CC=CC3=C1 UKOVZLWSUZKTRL-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/04—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines without replacement of the other oxygen atom of the carboxyl group, e.g. imino-ethers
- C07C257/06—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines without replacement of the other oxygen atom of the carboxyl group, e.g. imino-ethers having carbon atoms of imino-carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms, or to carbon atoms of rings other than six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUEE001239 | 1966-04-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH513130A true CH513130A (de) | 1971-09-30 |
Family
ID=10995190
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH562467A CH513130A (de) | 1966-04-21 | 1967-04-20 | Verfahren zur Herstellung von neuen N-Naphthyl- bzw. N-Tetrahydronaphthylformiminoäthern |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT268259B (enrdf_load_stackoverflow) |
| BE (1) | BE697217A (enrdf_load_stackoverflow) |
| CH (1) | CH513130A (enrdf_load_stackoverflow) |
| CS (1) | CS157030B2 (enrdf_load_stackoverflow) |
| DE (1) | DE1618310B2 (enrdf_load_stackoverflow) |
| DK (1) | DK124255B (enrdf_load_stackoverflow) |
| GB (1) | GB1158619A (enrdf_load_stackoverflow) |
| IL (1) | IL27806A (enrdf_load_stackoverflow) |
| NL (1) | NL151359B (enrdf_load_stackoverflow) |
| SE (1) | SE332977B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9962689B2 (en) | 2013-12-18 | 2018-05-08 | Chevron Phillips Chemical Company Lp | Phosphinyl formamidine compounds, metal complexes, catalyst systems, and their use to oligomerize or polymerize olefins |
-
1967
- 1967-04-13 AT AT347267A patent/AT268259B/de active
- 1967-04-13 DE DE1618310A patent/DE1618310B2/de active Granted
- 1967-04-17 GB GB17595/67A patent/GB1158619A/en not_active Expired
- 1967-04-17 IL IL27806A patent/IL27806A/xx unknown
- 1967-04-19 BE BE697217D patent/BE697217A/xx unknown
- 1967-04-20 NL NL676705576A patent/NL151359B/xx not_active IP Right Cessation
- 1967-04-20 CH CH562467A patent/CH513130A/de not_active IP Right Cessation
- 1967-04-20 DK DK214767AA patent/DK124255B/da unknown
- 1967-04-20 SE SE05566/67A patent/SE332977B/xx unknown
- 1967-04-21 CS CS292867A patent/CS157030B2/cs unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9962689B2 (en) | 2013-12-18 | 2018-05-08 | Chevron Phillips Chemical Company Lp | Phosphinyl formamidine compounds, metal complexes, catalyst systems, and their use to oligomerize or polymerize olefins |
Also Published As
| Publication number | Publication date |
|---|---|
| AT268259B (de) | 1969-02-10 |
| NL151359B (nl) | 1976-11-15 |
| DE1618310B2 (de) | 1974-03-21 |
| CS157030B2 (enrdf_load_stackoverflow) | 1974-08-23 |
| SE332977B (enrdf_load_stackoverflow) | 1971-03-01 |
| DK124255B (da) | 1972-10-02 |
| DE1618310C3 (enrdf_load_stackoverflow) | 1974-11-28 |
| DE1618310A1 (de) | 1971-03-11 |
| NL6705576A (enrdf_load_stackoverflow) | 1967-10-23 |
| BE697217A (enrdf_load_stackoverflow) | 1967-10-02 |
| IL27806A (en) | 1971-04-28 |
| GB1158619A (en) | 1969-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |