PL72620B1 - - Google Patents
Download PDFInfo
- Publication number
- PL72620B1 PL72620B1 PL13192369A PL13192369A PL72620B1 PL 72620 B1 PL72620 B1 PL 72620B1 PL 13192369 A PL13192369 A PL 13192369A PL 13192369 A PL13192369 A PL 13192369A PL 72620 B1 PL72620 B1 PL 72620B1
- Authority
- PL
- Poland
- Prior art keywords
- general formula
- reactions
- carried out
- water
- hal
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002527 isonitriles Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- XZUAPPXGIFNDRA-UHFFFAOYSA-N ethane-1,2-diamine;hydrate Chemical compound O.NCCN XZUAPPXGIFNDRA-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 102100033393 Anillin Human genes 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010021118 Hypotonia Diseases 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 108010061189 anillin Proteins 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical class C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- RCIBIGQXGCBBCT-UHFFFAOYSA-N phenyl isocyanide Chemical compound [C-]#[N+]C1=CC=CC=C1 RCIBIGQXGCBBCT-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000002271 resection Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD13292768 | 1968-06-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL72620B1 true PL72620B1 (cs) | 1974-08-30 |
Family
ID=5480092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL13192369A PL72620B1 (cs) | 1968-06-20 | 1969-02-24 |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT284838B (cs) |
| BG (1) | BG21097A2 (cs) |
| CH (1) | CH501644A (cs) |
| DK (1) | DK135588C (cs) |
| HU (1) | HU162517B (cs) |
| PL (1) | PL72620B1 (cs) |
| RO (1) | RO61582A (cs) |
| YU (1) | YU31837B (cs) |
-
1968
- 1968-07-23 AT AT713068A patent/AT284838B/de not_active IP Right Cessation
- 1968-08-10 BG BG1047868A patent/BG21097A2/xx unknown
- 1968-08-13 YU YU192668A patent/YU31837B/xx unknown
- 1968-08-27 DK DK411268A patent/DK135588C/da active
- 1968-11-08 CH CH1672868A patent/CH501644A/de not_active IP Right Cessation
-
1969
- 1969-02-07 HU HUAE000287 patent/HU162517B/hu unknown
- 1969-02-24 PL PL13192369A patent/PL72620B1/pl unknown
- 1969-03-03 RO RO6959247A patent/RO61582A/ro unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RO61582B (ro) | 1983-06-30 |
| DK135588B (da) | 1977-05-23 |
| YU31837B (en) | 1973-12-31 |
| YU192668A (en) | 1973-06-30 |
| HU162517B (cs) | 1973-03-28 |
| RO61582A (ro) | 1983-07-07 |
| CH501644A (de) | 1971-01-15 |
| DK135588C (da) | 1977-10-31 |
| BG21097A2 (cs) | 1976-03-20 |
| AT284838B (de) | 1970-09-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2410793T3 (es) | Nuevo procedimiento para la preparación de derivados de 2-imino-tiazolidin-4-ona | |
| FI59991B (fi) | Foerfarande foer framstaellning av 2-arylamino-2-imidazolin-derivat och deras salter | |
| KR102636758B1 (ko) | 치환된 벤조트라이아졸 페놀 | |
| CS198297B2 (en) | Method of producing derivatives of urea | |
| JPS632264B2 (cs) | ||
| PL72620B1 (cs) | ||
| PL207150B1 (pl) | Sposób wytwarzania pochodnych [1,4,5]- oksadiazepiny | |
| US4670558A (en) | Aminoalkylmelamines | |
| PL197776B1 (pl) | Sposób wytwarzania dichlorowodorku 1-[[[5-(4-chlorofenylo)-2-furanylo]metyleno]amino]-3-[4-(4-metylo-1-piperazynylo)butylo]-2,4-imidazolidynodionu | |
| US2729645A (en) | 1-[2-(dithiocarboxyamino)polymethylene] quaternary ammonium inner salts | |
| JP2678758B2 (ja) | 新規なプロパン誘導体 | |
| US2748120A (en) | 2-amino-6-aryl-5, 6-dihydro-4-hydroxy-pyrimidines | |
| US3226379A (en) | Novel 1,3-bis(polyhydroxyalkyl)-2-imidazolidinones and 1,3-bis(polyhydroxyalkyl)-imidazolidine-2-thiones | |
| PL164340B1 (pl) | Sposób wytwarzania nowych pochodnych benzotiazyny PL PL | |
| US1880447A (en) | Max haedtmann | |
| US4599428A (en) | Process for the preparation of 5(6)-thio substituted benzimidazoles | |
| US2570087A (en) | Process of preparing same | |
| SU640658A3 (ru) | Способ получени производных 2-амино индана или их кислых солей | |
| SU283934A1 (cs) | ||
| US2017976A (en) | Complex compound of alkali- and alkaline earth-metal halides | |
| SU488403A3 (ru) | Способ получени замещенной бензолсульфонилмочевины | |
| US4235819A (en) | Process for isolating 1-(alkoxyphenyl)-5-(phenyl)biguanide compounds from a crude, acid reaction mixture thereof | |
| PL104471B1 (pl) | Sposob wytwarzania pochodnych 1-karbamylouracylu | |
| SU247289A1 (ru) | Способ получения производных дифенилмочевины | |
| SU253685A1 (ru) | Способ получения замещенных карбоксамидотиазолов |