BE478523A - - Google Patents
Info
- Publication number
- BE478523A BE478523A BE478523DA BE478523A BE 478523 A BE478523 A BE 478523A BE 478523D A BE478523D A BE 478523DA BE 478523 A BE478523 A BE 478523A
- Authority
- BE
- Belgium
- Prior art keywords
- methyl
- imidazolidone
- phenyl
- hydrogenated
- group
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 26
- 238000005984 hydrogenation reaction Methods 0.000 claims description 20
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 14
- -1 3,4-dibenzyloxyphenyl Chemical group 0.000 claims description 13
- 150000004985 diamines Chemical class 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- 239000011780 sodium chloride Substances 0.000 claims description 8
- 230000000875 corresponding Effects 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 1,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims description 6
- IEOVAZVJCNUJPI-UHFFFAOYSA-N 1-phenylbutane-2,3-diamine Chemical compound CC(N)C(N)CC1=CC=CC=C1 IEOVAZVJCNUJPI-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 230000002378 acidificating Effects 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 3
- KBCCFPQJYAZWGA-UHFFFAOYSA-N 3,4-dimethyl-5-phenyl-1H-imidazol-2-one Chemical compound N1C(=O)N(C)C(C)=C1C1=CC=CC=C1 KBCCFPQJYAZWGA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000005354 acylalkyl group Chemical group 0.000 claims 3
- ISIJGZLHZALNDU-UHFFFAOYSA-N 2-N-methyl-1-phenylpropane-1,2-diamine Chemical compound CNC(C)C(N)C1=CC=CC=C1 ISIJGZLHZALNDU-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 79
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 75
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 49
- 238000002844 melting Methods 0.000 description 49
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- 239000000243 solution Substances 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 239000000203 mixture Substances 0.000 description 29
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 238000009835 boiling Methods 0.000 description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
- 229960000583 Acetic Acid Drugs 0.000 description 17
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 16
- 238000010992 reflux Methods 0.000 description 15
- 239000000126 substance Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 9
- 239000000155 melt Substances 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 230000001476 alcoholic Effects 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000005712 crystallization Effects 0.000 description 6
- 230000001376 precipitating Effects 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000000859 sublimation Methods 0.000 description 6
- 238000007792 addition Methods 0.000 description 5
- WZELXJBMMZFDDU-UHFFFAOYSA-N imidazol-2-one Chemical class O=C1N=CC=N1 WZELXJBMMZFDDU-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- ONZDMLLPTPDQAT-UHFFFAOYSA-N 3-phenylpropane-1,2-diamine;dihydrochloride Chemical compound Cl.Cl.NCC(N)CC1=CC=CC=C1 ONZDMLLPTPDQAT-UHFFFAOYSA-N 0.000 description 3
- WLRPOQVNDMDZEV-UHFFFAOYSA-N 4-benzoyl-5-methylimidazol-2-one Chemical compound CC1=NC(=O)N=C1C(=O)C1=CC=CC=C1 WLRPOQVNDMDZEV-UHFFFAOYSA-N 0.000 description 3
- ITCUMICAEDFLIL-UHFFFAOYSA-N 4-benzoylimidazol-2-one Chemical compound C=1C=CC=CC=1C(=O)C1=NC(=O)N=C1 ITCUMICAEDFLIL-UHFFFAOYSA-N 0.000 description 3
- GSQBXSXDPQFFOT-UHFFFAOYSA-N C1(CCCCC1)CC1NC(NC1)=O Chemical compound C1(CCCCC1)CC1NC(NC1)=O GSQBXSXDPQFFOT-UHFFFAOYSA-N 0.000 description 3
- NMCUIPGRVMDVDB-UHFFFAOYSA-L Iron(II) chloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 3
- GKKCIDNWFBPDBW-UHFFFAOYSA-M Potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M Sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000006640 acetylation reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- BGPAZBKCZVVZGF-UHFFFAOYSA-N 1,5-dimethyl-4-phenylimidazolidin-2-one Chemical compound N1C(=O)N(C)C(C)C1C1=CC=CC=C1 BGPAZBKCZVVZGF-UHFFFAOYSA-N 0.000 description 2
- LRNGDEHBVKSHOV-UHFFFAOYSA-N 1-cyclohexylbutane-2,3-diamine Chemical compound CC(N)C(N)CC1CCCCC1 LRNGDEHBVKSHOV-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N Benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- IAJWRZNYVRNODU-UHFFFAOYSA-N CC1=NC(=O)N=C1CC1=CC=CC=C1 Chemical compound CC1=NC(=O)N=C1CC1=CC=CC=C1 IAJWRZNYVRNODU-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical class [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N 1,2-ethanediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- VWFITDMAWXMPQO-UHFFFAOYSA-N 1,3-diacetyl-4-benzoyl-5-methylimidazol-2-one Chemical compound CC(=O)N1C(=O)N(C(=O)C)C(C)=C1C(=O)C1=CC=CC=C1 VWFITDMAWXMPQO-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CXFFQOZYXJHZNJ-UHFFFAOYSA-N 3-phenylpropane-1,2-diamine Chemical compound NCC(N)CC1=CC=CC=C1 CXFFQOZYXJHZNJ-UHFFFAOYSA-N 0.000 description 1
- PKMKZLLKQRSISH-UHFFFAOYSA-N 4-methyl-5-phenylimidazol-2-one Chemical compound CC1=NC(=O)N=C1C1=CC=CC=C1 PKMKZLLKQRSISH-UHFFFAOYSA-N 0.000 description 1
- JMVQFRFKXOIRBI-UHFFFAOYSA-N 4-methylimidazol-2-one Chemical compound CC1=NC(=O)N=C1 JMVQFRFKXOIRBI-UHFFFAOYSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N 5-(7-(4-(4,5-DIHYDRO-2-OXAZOLYL)PHENOXY)HEPTYL)-3-METHYL ISOXAZOLE Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- WNLPNKDYWRKPQV-UHFFFAOYSA-N C(C)(=O)N1C(N(C(=C1CC1=CC=CC=C1)C)C(C)=O)=O Chemical compound C(C)(=O)N1C(N(C(=C1CC1=CC=CC=C1)C)C(C)=O)=O WNLPNKDYWRKPQV-UHFFFAOYSA-N 0.000 description 1
- BAPDXUMEJAZMOL-UHFFFAOYSA-N C(C1=CC=CC=C1)C=1C(N=[C-]N=1)=O Chemical compound C(C1=CC=CC=C1)C=1C(N=[C-]N=1)=O BAPDXUMEJAZMOL-UHFFFAOYSA-N 0.000 description 1
- GRKHTSOKVDBEHR-UHFFFAOYSA-N CC1NC(NC1CC1CCCCC1)=O Chemical compound CC1NC(NC1CC1CCCCC1)=O GRKHTSOKVDBEHR-UHFFFAOYSA-N 0.000 description 1
- STZCRXQWRGQSJD-GEEYTBSJSA-M Methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
- 229940012189 Methyl orange Drugs 0.000 description 1
- 210000004940 Nucleus Anatomy 0.000 description 1
- 229940083599 Sodium Iodide Drugs 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000005574 benzylation reaction Methods 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000003301 hydrolyzing Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000926 not very toxic Toxicity 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000001184 potassium carbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
- 230000001131 transforming Effects 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE478523A true BE478523A (da) |
Family
ID=126256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE478523D BE478523A (da) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE478523A (da) |
-
0
- BE BE478523D patent/BE478523A/fr unknown
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