DE2056406A1 - Verfahren zur Herstellung von 1 Alkyl 4, 6 diphenylpynmidin 2(1H) onen - Google Patents
Verfahren zur Herstellung von 1 Alkyl 4, 6 diphenylpynmidin 2(1H) onenInfo
- Publication number
- DE2056406A1 DE2056406A1 DE19702056406 DE2056406A DE2056406A1 DE 2056406 A1 DE2056406 A1 DE 2056406A1 DE 19702056406 DE19702056406 DE 19702056406 DE 2056406 A DE2056406 A DE 2056406A DE 2056406 A1 DE2056406 A1 DE 2056406A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- alkyl
- above meaning
- ones
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 61
- 125000000217 alkyl group Chemical group 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 100
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 68
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- 239000003960 organic solvent Substances 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001350 alkyl halides Chemical class 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- YECVQOULKHBGEN-UHFFFAOYSA-N 1,3-diphenylprop-2-yn-1-one Chemical class C=1C=CC=CC=1C(=O)C#CC1=CC=CC=C1 YECVQOULKHBGEN-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- UVJQQYMWMAISMQ-UHFFFAOYSA-N ethyl 2,4-dioxo-4-phenylbutanoate Chemical compound CCOC(=O)C(=O)CC(=O)C1=CC=CC=C1 UVJQQYMWMAISMQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 1
- 235000013877 carbamide Nutrition 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- -1 nitro- Chemical class 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- 239000007858 starting material Substances 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 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 description 7
- 238000010992 reflux Methods 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 150000004292 cyclic ethers Chemical class 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- FJCQSNRTMHICQQ-UHFFFAOYSA-N 1-ethyl-4,6-diphenylpyrimidin-2-one Chemical compound N=1C(=O)N(CC)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 FJCQSNRTMHICQQ-UHFFFAOYSA-N 0.000 description 4
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- HVTASVIOKKMCLW-UHFFFAOYSA-N 4,6-diphenyl-1h-pyrimidin-2-one Chemical class N1C(=O)N=C(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 HVTASVIOKKMCLW-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000012730 sustained-release form Substances 0.000 description 4
- AERNUZQGYUISNN-UHFFFAOYSA-N 1-methyl-4,6-bis(3-methylphenyl)pyrimidin-2-one Chemical compound CC1=CC=CC(C2=NC(=O)N(C)C(C=3C=C(C)C=CC=3)=C2)=C1 AERNUZQGYUISNN-UHFFFAOYSA-N 0.000 description 3
- DKUIYFVMYQTXEA-UHFFFAOYSA-N 6-(4-methoxyphenyl)-1-methyl-4-phenylpyrimidin-2-one Chemical compound C1=CC(OC)=CC=C1C1=CC(C=2C=CC=CC=2)=NC(=O)N1C DKUIYFVMYQTXEA-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 238000006400 oxidative hydrolysis reaction Methods 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- UOZQLXATNWEWBI-UHFFFAOYSA-N 1-methyl-6-(3-nitrophenyl)-4-phenylpyrimidin-2-one Chemical compound N=1C(=O)N(C)C(C=2C=C(C=CC=2)[N+]([O-])=O)=CC=1C1=CC=CC=C1 UOZQLXATNWEWBI-UHFFFAOYSA-N 0.000 description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- HVYHGZUQAYFJJU-UHFFFAOYSA-N 4,6-bis(3-bromophenyl)-1-ethylpyrimidin-2-one Chemical compound N=1C(=O)N(CC)C(C=2C=C(Br)C=CC=2)=CC=1C1=CC=CC(Br)=C1 HVYHGZUQAYFJJU-UHFFFAOYSA-N 0.000 description 2
- UCEHZDJROOEPOW-UHFFFAOYSA-N 4,6-bis(3-chlorophenyl)-1-methylpyrimidin-2-one Chemical compound N=1C(=O)N(C)C(C=2C=C(Cl)C=CC=2)=CC=1C1=CC=CC(Cl)=C1 UCEHZDJROOEPOW-UHFFFAOYSA-N 0.000 description 2
- JQVIRXYVNFLRTH-UHFFFAOYSA-N 4,6-diphenyl-1-propan-2-ylpyrimidin-2-one Chemical compound N=1C(=O)N(C(C)C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 JQVIRXYVNFLRTH-UHFFFAOYSA-N 0.000 description 2
- GJHYBWSQPJJAAT-UHFFFAOYSA-N 4,6-diphenyl-1-propylpyrimidin-2-one Chemical compound N=1C(=O)N(CCC)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 GJHYBWSQPJJAAT-UHFFFAOYSA-N 0.000 description 2
- DSPQUJVQJJZLNA-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-1-methyl-4-phenylpyrimidin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(C=2C=CC=CC=2)=NC(=O)N1C DSPQUJVQJJZLNA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LVVWUIYIQAHKQQ-UHFFFAOYSA-N ClC=1C(=C(C(=C(C(=O)C2=CC=CC=C2)C=1)C#N)C#N)Cl Chemical compound ClC=1C(=C(C(=C(C(=O)C2=CC=CC=C2)C=1)C#N)C#N)Cl LVVWUIYIQAHKQQ-UHFFFAOYSA-N 0.000 description 2
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methyl urea Chemical compound CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241001061127 Thione Species 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 241001233037 catfish Species 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical class C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000000147 hypnotic effect Effects 0.000 description 2
- 150000002642 lithium compounds Chemical class 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 2
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- MGMNGNDIJHTGOF-UHFFFAOYSA-N 1,3-bis(3-chlorophenyl)propane-1,3-dione Chemical compound ClC1=CC=CC(C(=O)CC(=O)C=2C=C(Cl)C=CC=2)=C1 MGMNGNDIJHTGOF-UHFFFAOYSA-N 0.000 description 1
- WQUXFYFIXPSYGK-UHFFFAOYSA-N 1-butyl-4,6-diphenylpyrimidin-2-one Chemical compound N=1C(=O)N(CCCC)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 WQUXFYFIXPSYGK-UHFFFAOYSA-N 0.000 description 1
- MBKHINORQZYOII-UHFFFAOYSA-N 1-ethyl-4,6-diphenylpyrimidine-2-thione Chemical compound C(C)N1C(N=C(C=C1C1=CC=CC=C1)C1=CC=CC=C1)=S MBKHINORQZYOII-UHFFFAOYSA-N 0.000 description 1
- JAMITZDZMVAWEO-UHFFFAOYSA-N 1-ethyl-4-(3-methoxyphenyl)-6-(3-nitrophenyl)pyrimidin-2-one Chemical compound N=1C(=O)N(CC)C(C=2C=C(C=CC=2)[N+]([O-])=O)=CC=1C1=CC=CC(OC)=C1 JAMITZDZMVAWEO-UHFFFAOYSA-N 0.000 description 1
- ULZHFSLOIIOYAP-UHFFFAOYSA-N 1-ethyl-6-(3-methoxyphenyl)-4-(3-nitrophenyl)pyrimidin-2-one Chemical compound N=1C(=O)N(CC)C(C=2C=C(OC)C=CC=2)=CC=1C1=CC=CC([N+]([O-])=O)=C1 ULZHFSLOIIOYAP-UHFFFAOYSA-N 0.000 description 1
- ZKCPQPJBBHHDES-UHFFFAOYSA-N 1-ethyl-6-phenylpyrimidin-2-one Chemical compound C(C)N1C(N=CC=C1C1=CC=CC=C1)=O ZKCPQPJBBHHDES-UHFFFAOYSA-N 0.000 description 1
- SLGOWNPJQDMMTE-UHFFFAOYSA-N 1-methyl-4,6-diphenylpyrimidin-2-one Chemical compound N=1C(=O)N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 SLGOWNPJQDMMTE-UHFFFAOYSA-N 0.000 description 1
- FADDGUDTESIUNX-UHFFFAOYSA-N 1-phenylpyrimidin-2-one Chemical compound O=C1N=CC=CN1C1=CC=CC=C1 FADDGUDTESIUNX-UHFFFAOYSA-N 0.000 description 1
- QGKGASXQTBQINX-UHFFFAOYSA-N 3,4-dihydro-1h-pyrimidin-2-one Chemical class O=C1NCC=CN1 QGKGASXQTBQINX-UHFFFAOYSA-N 0.000 description 1
- DNXUGBMARDFRGG-UHFFFAOYSA-N 3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile Chemical compound O=C1C=CC(=O)C(C#N)=C1C#N DNXUGBMARDFRGG-UHFFFAOYSA-N 0.000 description 1
- WRFPKYHCEGXPHI-UHFFFAOYSA-N 3-(ethylamino)-1,3-diphenylpropan-1-one Chemical compound C1(=CC=CC=C1)C(CC(=O)C1=CC=CC=C1)NCC WRFPKYHCEGXPHI-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- VMZVSRLEMFTZTQ-UHFFFAOYSA-N 6-(3-chlorophenyl)-1-methyl-4-phenylpyrimidin-2-one Chemical compound CN1C(N=C(C=C1C1=CC(=CC=C1)Cl)C1=CC=CC=C1)=O VMZVSRLEMFTZTQ-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- GUHTYFMKNHVDTN-UHFFFAOYSA-N C(C)N1C(N=C(C=C1C1=CC=CC=C1)C1=CC(=CC=C1)C(F)(F)F)=O Chemical compound C(C)N1C(N=C(C=C1C1=CC=CC=C1)C1=CC(=CC=C1)C(F)(F)F)=O GUHTYFMKNHVDTN-UHFFFAOYSA-N 0.000 description 1
- FIMNKUHLZAOUNQ-UHFFFAOYSA-N C(C)N1C(NC(=CC1C1=CC(=CC=C1)OC)C1=CC(=CC=C1)[N+](=O)[O-])=O Chemical compound C(C)N1C(NC(=CC1C1=CC(=CC=C1)OC)C1=CC(=CC=C1)[N+](=O)[O-])=O FIMNKUHLZAOUNQ-UHFFFAOYSA-N 0.000 description 1
- CEQMWEKWFJHHKY-UHFFFAOYSA-N C(C)N1C(NC(=CC1C1=CC(=CC=C1)[N+](=O)[O-])C1=CC(=CC=C1)OC)=O Chemical compound C(C)N1C(NC(=CC1C1=CC(=CC=C1)[N+](=O)[O-])C1=CC(=CC=C1)OC)=O CEQMWEKWFJHHKY-UHFFFAOYSA-N 0.000 description 1
- GTPXHNRVDOPRME-UHFFFAOYSA-N CCN(C(C1=CC=CC=C1)=CC(C1=CC(C)=CC=C1)=N1)C1=O Chemical compound CCN(C(C1=CC=CC=C1)=CC(C1=CC(C)=CC=C1)=N1)C1=O GTPXHNRVDOPRME-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- GMEHFXXZSWDEDB-UHFFFAOYSA-N N-ethylthiourea Chemical compound CCNC(N)=S GMEHFXXZSWDEDB-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 1
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- LTIBQZLAXJMKEF-UHFFFAOYSA-N azane;isocyanic acid Chemical compound N.N=C=O LTIBQZLAXJMKEF-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- JLCRXCPXQLBSEM-UHFFFAOYSA-N calcium diisocyanate Chemical compound [Ca++].[N-]=C=O.[N-]=C=O JLCRXCPXQLBSEM-UHFFFAOYSA-N 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- RFAKLMBNSZNUNX-UHFFFAOYSA-N potassium;isothiocyanate Chemical compound [K+].[N-]=C=S RFAKLMBNSZNUNX-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/516—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of nitrogen-containing compounds to >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/26—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups
- C07C47/27—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
- C07D239/40—One sulfur atom as doubly bound sulfur atom or as unsubstituted mercapto radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87857269A | 1969-11-20 | 1969-11-20 | |
| US3734170A | 1970-05-14 | 1970-05-14 | |
| US8822270A | 1970-11-09 | 1970-11-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2056406A1 true DE2056406A1 (de) | 1971-05-27 |
Family
ID=27365196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702056406 Pending DE2056406A1 (de) | 1969-11-20 | 1970-11-17 | Verfahren zur Herstellung von 1 Alkyl 4, 6 diphenylpynmidin 2(1H) onen |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE759123A (enrdf_load_stackoverflow) |
| CA (1) | CA962272A (enrdf_load_stackoverflow) |
| DE (1) | DE2056406A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2077528B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1328857A (enrdf_load_stackoverflow) |
| NL (1) | NL7016977A (enrdf_load_stackoverflow) |
| OA (1) | OA03525A (enrdf_load_stackoverflow) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE626980A (enrdf_load_stackoverflow) * | 1962-01-10 |
-
0
- BE BE759123D patent/BE759123A/xx unknown
-
1970
- 1970-11-09 GB GB5318670A patent/GB1328857A/en not_active Expired
- 1970-11-17 DE DE19702056406 patent/DE2056406A1/de active Pending
- 1970-11-18 OA OA54092A patent/OA03525A/xx unknown
- 1970-11-18 FR FR707041336A patent/FR2077528B1/fr not_active Expired
- 1970-11-19 CA CA098,559A patent/CA962272A/en not_active Expired
- 1970-11-19 NL NL7016977A patent/NL7016977A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7016977A (enrdf_load_stackoverflow) | 1971-05-24 |
| GB1328857A (en) | 1973-09-05 |
| FR2077528B1 (enrdf_load_stackoverflow) | 1974-02-15 |
| FR2077528A1 (enrdf_load_stackoverflow) | 1971-10-29 |
| BE759123A (fr) | 1971-05-18 |
| OA03525A (fr) | 1971-03-30 |
| CA962272A (en) | 1975-02-04 |
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