SU422137A3 - Способ получения 1- - Google Patents
Способ получения 1-Info
- Publication number
- SU422137A3 SU422137A3 SU1705731A SU1705731A SU422137A3 SU 422137 A3 SU422137 A3 SU 422137A3 SU 1705731 A SU1705731 A SU 1705731A SU 1705731 A SU1705731 A SU 1705731A SU 422137 A3 SU422137 A3 SU 422137A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- hydrochloride
- methylphenoxy
- chloroform
- solution
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 10
- 229910001868 water Inorganic materials 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- -1 2-cyano-5-methylphenoxy Chemical group 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000001766 physiological effect Effects 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- LNSCNEJNLACZPA-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(2-methylphenyl)butanedioic acid Chemical compound CC1=CC=CC=C1C(O)(C(O)=O)C(O)(C(O)=O)C1=CC=CC=C1C LNSCNEJNLACZPA-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- VXIDBKBIIFWZHF-UHFFFAOYSA-N CC(C)(C)NCC(COC(C=C(C)C=C1)=C1N)O.Cl.Cl Chemical compound CC(C)(C)NCC(COC(C=C(C)C=C1)=C1N)O.Cl.Cl VXIDBKBIIFWZHF-UHFFFAOYSA-N 0.000 description 1
- KHAHNSYDGLCSBO-UHFFFAOYSA-N CC(C)NCC(COC(C=C(C)C=C1)=C1N)O.Cl.Cl Chemical compound CC(C)NCC(COC(C=C(C)C=C1)=C1N)O.Cl.Cl KHAHNSYDGLCSBO-UHFFFAOYSA-N 0.000 description 1
- OBHJEQFRDSQQSN-UHFFFAOYSA-N CCC(C)(C)NCC(COC(C=C(C)C=C1)=C1N)O.Cl.Cl Chemical compound CCC(C)(C)NCC(COC(C=C(C)C=C1)=C1N)O.Cl.Cl OBHJEQFRDSQQSN-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical group N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical class CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/275—Nitriles; Isonitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
-
- E—FIXED CONSTRUCTIONS
- E05—LOCKS; KEYS; WINDOW OR DOOR FITTINGS; SAFES
- E05D—HINGES OR SUSPENSION DEVICES FOR DOORS, WINDOWS OR WINGS
- E05D15/00—Suspension arrangements for wings
- E05D15/40—Suspension arrangements for wings supported on arms movable in vertical planes
- E05D15/44—Suspension arrangements for wings supported on arms movable in vertical planes with pivoted arms and vertically-sliding guides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Mechanical Engineering (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691950351 DE1950351C3 (de) | 1969-10-06 | 1969-10-06 | l-(2-Cyano-5-methylphenoxy)-2-hydroxy-3-aIkylaminopropane, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU422137A3 true SU422137A3 (ru) | 1974-03-30 |
Family
ID=5747463
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1705731A SU422137A3 (ru) | 1969-10-06 | 1970-10-05 | Способ получения 1- |
| SU1699774A SU426360A3 (ru) | 1969-10-06 | 1970-10-05 | Способ получения 1- |
| SU1705732A SU423291A3 (https=) | 1969-10-06 | 1970-10-05 | |
| SU1705733A SU421182A3 (ru) | 1969-10-06 | 1970-10-05 | Способ получения 1- |
| SU1705730A SU417938A3 (ru) | 1969-10-06 | 1970-10-05 | Способ получения 1- |
| SU1699773A SU503507A3 (ru) | 1969-10-06 | 1971-09-21 | Способ получени 1-(2-циано-5-метилфенокси)-2-окси-3-алкиламинопропанов |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1699774A SU426360A3 (ru) | 1969-10-06 | 1970-10-05 | Способ получения 1- |
| SU1705732A SU423291A3 (https=) | 1969-10-06 | 1970-10-05 | |
| SU1705733A SU421182A3 (ru) | 1969-10-06 | 1970-10-05 | Способ получения 1- |
| SU1705730A SU417938A3 (ru) | 1969-10-06 | 1970-10-05 | Способ получения 1- |
| SU1699773A SU503507A3 (ru) | 1969-10-06 | 1971-09-21 | Способ получени 1-(2-циано-5-метилфенокси)-2-окси-3-алкиламинопропанов |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS501262B1 (https=) |
| AT (10) | AT308072B (https=) |
| BG (8) | BG17528A3 (https=) |
| CH (1) | CH542814A (https=) |
| CS (1) | CS162731B2 (https=) |
| DE (1) | DE1950351C3 (https=) |
| DK (1) | DK128237B (https=) |
| ES (9) | ES384244A1 (https=) |
| PL (3) | PL84642B1 (https=) |
| RO (9) | RO59186A (https=) |
| SE (1) | SE375094B (https=) |
| SU (6) | SU422137A3 (https=) |
| YU (1) | YU34516B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2660811C1 (ru) * | 2017-03-21 | 2018-07-10 | Общество с ограниченной ответственностью Научно-производственное предприятие "Резонанс" (ООО НПП "Резонанс") | Индукторная электрическая машина |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI101950B1 (fi) | 1996-12-12 | 1998-09-30 | Uponor Bv | Menetelmä ja laitteisto kierrätettävän muovimateriaalin hyödyntämiseksi ja puristinlaitteella tehty muovituote |
-
1969
- 1969-10-02 BG BG018263A patent/BG17528A3/xx unknown
- 1969-10-06 DE DE19691950351 patent/DE1950351C3/de not_active Expired
-
1970
- 1970-09-23 CS CS646770A patent/CS162731B2/cs unknown
- 1970-10-02 BG BG018262A patent/BG17294A3/xx unknown
- 1970-10-02 BG BG018264A patent/BG17295A3/xx unknown
- 1970-10-02 BG BG018265A patent/BG17296A3/xx unknown
- 1970-10-02 CH CH1461770A patent/CH542814A/de not_active IP Right Cessation
- 1970-10-02 BG BG018261A patent/BG17527A3/xx unknown
- 1970-10-02 BG BG018266A patent/BG17529A3/xx unknown
- 1970-10-02 BG BG015776A patent/BG17293A3/xx unknown
- 1970-10-02 BG BG018268A patent/BG17531A3/xx unknown
- 1970-10-03 ES ES384244A patent/ES384244A1/es not_active Expired
- 1970-10-05 SE SE1347570A patent/SE375094B/xx unknown
- 1970-10-05 DK DK505570A patent/DK128237B/da not_active IP Right Cessation
- 1970-10-05 JP JP8675670A patent/JPS501262B1/ja active Pending
- 1970-10-05 SU SU1705731A patent/SU422137A3/ru active
- 1970-10-05 PL PL17334270A patent/PL84642B1/pl unknown
- 1970-10-05 SU SU1699774A patent/SU426360A3/ru active
- 1970-10-05 PL PL14378570A patent/PL84252B1/pl unknown
- 1970-10-05 YU YU244470A patent/YU34516B/xx unknown
- 1970-10-05 SU SU1705732A patent/SU423291A3/ru active
- 1970-10-05 PL PL17334370A patent/PL84637B1/pl unknown
- 1970-10-05 SU SU1705733A patent/SU421182A3/ru active
- 1970-10-05 SU SU1705730A patent/SU417938A3/ru active
- 1970-10-06 AT AT1052371A patent/AT308072B/de not_active IP Right Cessation
- 1970-10-06 AT AT1052571A patent/AT306695B/de not_active IP Right Cessation
- 1970-10-06 RO RO6727170A patent/RO59186A/ro unknown
- 1970-10-06 RO RO6727270A patent/RO58534A/ro unknown
- 1970-10-06 AT AT1053071A patent/AT306700B/de not_active IP Right Cessation
- 1970-10-06 AT AT900970A patent/AT302274B/de not_active IP Right Cessation
- 1970-10-06 RO RO6726870A patent/RO58532A/ro unknown
- 1970-10-06 AT AT1052871A patent/AT306698B/de not_active IP Right Cessation
- 1970-10-06 AT AT1052671A patent/AT306696B/de not_active IP Right Cessation
- 1970-10-06 AT AT1053171A patent/AT306701B/de not_active IP Right Cessation
- 1970-10-06 AT AT1052771A patent/AT306697B/de not_active IP Right Cessation
- 1970-10-06 RO RO6461670A patent/RO56983A/ro unknown
- 1970-10-06 RO RO6726970A patent/RO59185A/ro unknown
- 1970-10-06 RO RO6728970A patent/RO58550A/ro unknown
- 1970-10-06 RO RO6727070A patent/RO58533A/ro unknown
- 1970-10-06 AT AT1052971A patent/AT306699B/de not_active IP Right Cessation
- 1970-10-06 RO RO6727370A patent/RO58548A/ro unknown
- 1970-10-06 AT AT1052471A patent/AT306694B/de not_active IP Right Cessation
- 1970-10-06 RO RO6727470A patent/RO58549A/ro unknown
-
1971
- 1971-05-13 ES ES391137A patent/ES391137A1/es not_active Expired
- 1971-05-13 ES ES391141A patent/ES391141A1/es not_active Expired
- 1971-05-13 ES ES391138A patent/ES391138A1/es not_active Expired
- 1971-05-13 ES ES391136A patent/ES391136A1/es not_active Expired
- 1971-05-13 ES ES391135A patent/ES391135A1/es not_active Expired
- 1971-05-13 ES ES391139A patent/ES391139A1/es not_active Expired
- 1971-05-13 ES ES391134A patent/ES391134A1/es not_active Expired
- 1971-05-13 ES ES391140A patent/ES391140A1/es not_active Expired
- 1971-09-21 SU SU1699773A patent/SU503507A3/ru active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2660811C1 (ru) * | 2017-03-21 | 2018-07-10 | Общество с ограниченной ответственностью Научно-производственное предприятие "Резонанс" (ООО НПП "Резонанс") | Индукторная электрическая машина |
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