SU293341A1 - - Google Patents

Info

Publication number

SU293341A1

SU293341A1 SU1190702A SU1190702A SU293341A1 SU 293341 A1 SU293341 A1 SU 293341A1 SU 1190702 A SU1190702 A SU 1190702A SU 1190702 A SU1190702 A SU 1190702A SU 293341 A1 SU293341 A1 SU 293341A1

Authority

SU

USSR - Soviet Union

Prior art keywords

ethyl

alkyl

carbon atoms

benzenesulfonyl

methoxy

Prior art date

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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
• 125000000217 alkyl group Chemical group 0.000 description 11
• 125000004432 carbon atom Chemical group C* 0.000 description 9
• -1 methoxyethyl Chemical group 0.000 description 9
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
• 238000000034 method Methods 0.000 description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
• 150000003839 salts Chemical class 0.000 description 3
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
• 239000002253 acid Substances 0.000 description 2
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
• 125000003342 alkenyl group Chemical group 0.000 description 2
• 125000003545 alkoxy group Chemical group 0.000 description 2
• 150000001412 amines Chemical class 0.000 description 2
• 239000004202 carbamide Substances 0.000 description 2
• 229910052801 chlorine Inorganic materials 0.000 description 2
• 239000000460 chlorine Substances 0.000 description 2
• 125000000753 cycloalkyl group Chemical group 0.000 description 2
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
• 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
• 229910052736 halogen Inorganic materials 0.000 description 2
• 150000002367 halogens Chemical group 0.000 description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• 230000020477 pH reduction Effects 0.000 description 2
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
• 238000010992 reflux Methods 0.000 description 2
• 150000007659 semicarbazones Chemical class 0.000 description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
• MMCNDPVHBALJKB-UHFFFAOYSA-N COC(C=CC(Cl)=C1)=C1C(NCCC(C=C1)=CC=C1S(NC(N)=O)(=O)=O)=S Chemical compound COC(C=CC(Cl)=C1)=C1C(NCCC(C=C1)=CC=C1S(NC(N)=O)(=O)=O)=S MMCNDPVHBALJKB-UHFFFAOYSA-N 0.000 description 1
• 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
• 235000011941 Tilia x europaea Nutrition 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 230000003993 interaction Effects 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 239000004571 lime Substances 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 238000002360 preparation method Methods 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• VNMLVHLVBFHHSN-UHFFFAOYSA-N thiophen-2-ylcarbamic acid Chemical class OC(=O)NC1=CC=CS1 VNMLVHLVBFHHSN-UHFFFAOYSA-N 0.000 description 1
• KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
• 239000008096 xylene Substances 0.000 description 1