BE441809A - - Google Patents

Info

Publication number

BE441809A

BE441809A BE441809DA BE441809A BE 441809 A BE441809 A BE 441809A BE 441809D A BE441809D A BE 441809DA BE 441809 A BE441809 A BE 441809A

Authority

BE

Belgium

Prior art keywords

formic acid

methyl2

methyl

tetrahydrofuran

oxy

Prior art date

Links

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• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 44
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 22
• 235000019253 formic acid Nutrition 0.000 claims description 22
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
• 238000002360 preparation method Methods 0.000 claims description 10
• 239000011691 vitamin B1 Substances 0.000 claims description 10
• 235000010374 vitamin B1 Nutrition 0.000 claims description 10
• 150000001875 compounds Chemical class 0.000 claims description 8
• 238000006243 chemical reaction Methods 0.000 claims description 7
• 238000000034 method Methods 0.000 claims description 7
• -1 formyl-oxY Chemical class 0.000 claims description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• 150000003839 salts Chemical class 0.000 claims description 4
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
• 230000009466 transformation Effects 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims 1
• 150000003230 pyrimidines Chemical class 0.000 claims 1
• 229930003451 Vitamin B1 Natural products 0.000 description 9
• 229960003495 thiamine Drugs 0.000 description 9
• DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 9
• 239000000203 mixture Substances 0.000 description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
• 239000000460 chlorine Substances 0.000 description 3
• 229910052801 chlorine Inorganic materials 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• 239000000155 melt Substances 0.000 description 3
• QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
• 229910052753 mercury Inorganic materials 0.000 description 3
• 239000011782 vitamin Substances 0.000 description 3
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
• 229930003270 Vitamin B Natural products 0.000 description 2
• 239000002253 acid Substances 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• 238000009833 condensation Methods 0.000 description 2
• 230000005494 condensation Effects 0.000 description 2
• 239000013078 crystal Substances 0.000 description 2
• WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 2
• 238000010992 reflux Methods 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• 229930003231 vitamin Natural products 0.000 description 2
• 235000013343 vitamin Nutrition 0.000 description 2
• 229940088594 vitamin Drugs 0.000 description 2
• 235000019156 vitamin B Nutrition 0.000 description 2
• 239000011720 vitamin B Substances 0.000 description 2
• 150000003722 vitamin derivatives Chemical class 0.000 description 2
• OTVHLJOZEPOFMW-UHFFFAOYSA-N 2H-pyran-5-carboximidamide Chemical compound O1CC=CC(=C1)C(=N)N OTVHLJOZEPOFMW-UHFFFAOYSA-N 0.000 description 1
• WIGIZIANZCJQQY-UHFFFAOYSA-N 4-ethyl-3-methyl-N-[2-[4-[[[(4-methylcyclohexyl)amino]-oxomethyl]sulfamoyl]phenyl]ethyl]-5-oxo-2H-pyrrole-1-carboxamide Chemical compound O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCC(C)CC2)C=C1 WIGIZIANZCJQQY-UHFFFAOYSA-N 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
• 241000212342 Sium Species 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 238000004508 fractional distillation Methods 0.000 description 1
• 238000005194 fractionation Methods 0.000 description 1
• 150000002240 furans Chemical class 0.000 description 1
• 230000005484 gravity Effects 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 229940075930 picrate Drugs 0.000 description 1
• OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 239000012429 reaction media Substances 0.000 description 1
• 238000010626 work up procedure Methods 0.000 description 1