SU648089A3 - Способ получени 2,6-диацилоксиметилпиридинов - Google Patents
Способ получени 2,6-диацилоксиметилпиридиновInfo
- Publication number
- SU648089A3 SU648089A3 SU762341201A SU2341201A SU648089A3 SU 648089 A3 SU648089 A3 SU 648089A3 SU 762341201 A SU762341201 A SU 762341201A SU 2341201 A SU2341201 A SU 2341201A SU 648089 A3 SU648089 A3 SU 648089A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mol
- solvent
- yield
- reaction
- product
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 23
- 239000000047 product Substances 0.000 claims description 17
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 15
- 239000011541 reaction mixture Substances 0.000 claims 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 11
- 239000002904 solvent Substances 0.000 claims 11
- 238000006243 chemical reaction Methods 0.000 claims 10
- 239000000243 solution Substances 0.000 claims 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 8
- 238000009835 boiling Methods 0.000 claims 7
- 239000003921 oil Substances 0.000 claims 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 6
- 229960000583 acetic acid Drugs 0.000 claims 5
- 229940086542 triethylamine Drugs 0.000 claims 5
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims 4
- IWQNFYRJSVJWQA-UHFFFAOYSA-N 2,6-bis(chloromethyl)pyridine Chemical compound ClCC1=CC=CC(CCl)=N1 IWQNFYRJSVJWQA-UHFFFAOYSA-N 0.000 claims 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 4
- 238000001914 filtration Methods 0.000 claims 4
- 239000012362 glacial acetic acid Substances 0.000 claims 4
- 239000003960 organic solvent Substances 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000002026 chloroform extract Substances 0.000 claims 3
- 239000000706 filtrate Substances 0.000 claims 3
- 239000007789 gas Substances 0.000 claims 3
- 238000004817 gas chromatography Methods 0.000 claims 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical group 0.000 claims 3
- 239000007787 solid Substances 0.000 claims 3
- 150000003512 tertiary amines Chemical class 0.000 claims 3
- 238000004809 thin layer chromatography Methods 0.000 claims 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- XARIFKSEVODEFM-UHFFFAOYSA-N [6-(acetyloxymethyl)pyridin-2-yl]methyl acetate Chemical compound C(C)(=O)OCC1=NC(=CC=C1)COC(C)=O XARIFKSEVODEFM-UHFFFAOYSA-N 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 239000003610 charcoal Substances 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 230000007935 neutral effect Effects 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 2
- 239000000376 reactant Substances 0.000 claims 2
- 230000035484 reaction time Effects 0.000 claims 2
- 125000005270 trialkylamine group Chemical group 0.000 claims 2
- 238000000870 ultraviolet spectroscopy Methods 0.000 claims 2
- QUTSYCOAZVHGGT-UHFFFAOYSA-N 2,6-bis(bromomethyl)pyridine Chemical compound BrCC1=CC=CC(CBr)=N1 QUTSYCOAZVHGGT-UHFFFAOYSA-N 0.000 claims 1
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 102000007469 Actins Human genes 0.000 claims 1
- 108010085238 Actins Proteins 0.000 claims 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 1
- 239000001736 Calcium glycerylphosphate Substances 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 1
- 101100073352 Streptomyces halstedii sch1 gene Proteins 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 238000004458 analytical method Methods 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 238000004364 calculation method Methods 0.000 claims 1
- 150000001720 carbohydrates Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- HFNQLYDPNAZRCH-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O.OC(O)=O HFNQLYDPNAZRCH-UHFFFAOYSA-N 0.000 claims 1
- 239000012159 carrier gas Substances 0.000 claims 1
- 235000013351 cheese Nutrition 0.000 claims 1
- 238000004140 cleaning Methods 0.000 claims 1
- 239000012230 colorless oil Substances 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 238000005516 engineering process Methods 0.000 claims 1
- 239000000284 extract Substances 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 238000004508 fractional distillation Methods 0.000 claims 1
- 239000011521 glass Substances 0.000 claims 1
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical group O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- -1 however Chemical compound 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 238000011835 investigation Methods 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- KGCNHWXDPDPSBV-UHFFFAOYSA-N p-nitrobenzyl chloride Chemical compound [O-][N+](=O)C1=CC=C(CCl)C=C1 KGCNHWXDPDPSBV-UHFFFAOYSA-N 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 150000001204 N-oxides Chemical class 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- LVPMIMZXDYBCDF-UHFFFAOYSA-N isocinchomeronic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)N=C1 LVPMIMZXDYBCDF-UHFFFAOYSA-N 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N pyridinedicarboxylic acid Natural products OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HURI000562 HU170496B (enrdf_load_stackoverflow) | 1975-04-02 | 1975-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU648089A3 true SU648089A3 (ru) | 1979-02-15 |
Family
ID=11000971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762341201A SU648089A3 (ru) | 1975-04-02 | 1976-04-02 | Способ получени 2,6-диацилоксиметилпиридинов |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT347462B (enrdf_load_stackoverflow) |
| CH (1) | CH601236A5 (enrdf_load_stackoverflow) |
| CS (1) | CS207355B2 (enrdf_load_stackoverflow) |
| DD (1) | DD124875A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2614400C3 (enrdf_load_stackoverflow) |
| ES (1) | ES446523A1 (enrdf_load_stackoverflow) |
| HU (1) | HU170496B (enrdf_load_stackoverflow) |
| PL (1) | PL101309B1 (enrdf_load_stackoverflow) |
| SU (1) | SU648089A3 (enrdf_load_stackoverflow) |
| YU (1) | YU83776A (enrdf_load_stackoverflow) |
-
1975
- 1975-04-02 HU HURI000562 patent/HU170496B/hu unknown
-
1976
- 1976-03-25 CH CH376376A patent/CH601236A5/xx not_active IP Right Cessation
- 1976-03-29 AT AT225876A patent/AT347462B/de not_active IP Right Cessation
- 1976-03-31 ES ES446523A patent/ES446523A1/es not_active Expired
- 1976-03-31 CS CS207376A patent/CS207355B2/cs unknown
- 1976-04-01 YU YU83776A patent/YU83776A/xx unknown
- 1976-04-01 DD DD19216576A patent/DD124875A5/xx unknown
- 1976-04-01 PL PL18842276A patent/PL101309B1/pl unknown
- 1976-04-02 DE DE19762614400 patent/DE2614400C3/de not_active Expired
- 1976-04-02 SU SU762341201A patent/SU648089A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| ES446523A1 (es) | 1977-06-16 |
| YU83776A (en) | 1982-02-28 |
| CS207355B2 (en) | 1981-07-31 |
| DD124875A5 (enrdf_load_stackoverflow) | 1977-03-16 |
| ATA225876A (de) | 1978-05-15 |
| DE2614400C3 (de) | 1979-03-15 |
| PL101309B1 (pl) | 1978-12-30 |
| DE2614400A1 (de) | 1977-03-03 |
| HU170496B (enrdf_load_stackoverflow) | 1977-06-28 |
| AT347462B (de) | 1978-12-27 |
| CH601236A5 (enrdf_load_stackoverflow) | 1978-06-30 |
| DE2614400B2 (de) | 1978-07-06 |
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