BE485826A - - Google Patents

Info

Publication number

BE485826A

BE485826A BE485826DA BE485826A BE 485826 A BE485826 A BE 485826A BE 485826D A BE485826D A BE 485826DA BE 485826 A BE485826 A BE 485826A

Authority

BE

Belgium

Prior art keywords

parts

diphenyl

alkyl

chloro

hydrochloride

Prior art date

Links

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• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 9
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
• NFHKZAUDRWRXMZ-UHFFFAOYSA-N 2-chloro-2,2-diphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)Cl)C1=CC=CC=C1 NFHKZAUDRWRXMZ-UHFFFAOYSA-N 0.000 claims description 8
• -1 polymethylene chain Polymers 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• 238000000034 method Methods 0.000 claims description 4
• 239000000460 chlorine Substances 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 3
• 238000002360 preparation method Methods 0.000 claims description 3
• DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical class CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 claims description 3
• 125000004432 carbon atoms Chemical group C* 0.000 claims description 2
• 238000010438 heat treatment Methods 0.000 claims description 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
• 125000004430 oxygen atoms Chemical group O* 0.000 claims description 2
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000001309 chloro group Chemical group Cl* 0.000 claims 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 26
• VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• 238000002844 melting Methods 0.000 description 13
• 239000000203 mixture Substances 0.000 description 8
• 238000009835 boiling Methods 0.000 description 7
• 235000019441 ethanol Nutrition 0.000 description 7
• 239000002244 precipitate Substances 0.000 description 7
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• 239000003208 petroleum Substances 0.000 description 5
• 238000004821 distillation Methods 0.000 description 3
• 239000000155 melt Substances 0.000 description 3
• 238000001953 recrystallisation Methods 0.000 description 3
• 238000010992 reflux Methods 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
• 238000001035 drying Methods 0.000 description 2
• 150000003840 hydrochlorides Chemical class 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
• 239000000047 product Substances 0.000 description 2
• 229910052938 sodium sulfate Inorganic materials 0.000 description 2
• 235000011152 sodium sulphate Nutrition 0.000 description 2
• 150000003573 thiols Chemical class 0.000 description 2
• MBNVSWHUJDDZRH-UHFFFAOYSA-N 2-methylthiirane Chemical compound CC1CS1 MBNVSWHUJDDZRH-UHFFFAOYSA-N 0.000 description 1
• KZTSRNUHHDHDTD-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(=O)Br)(Cl)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C(C(=O)Br)(Cl)C1=CC=CC=C1 KZTSRNUHHDHDTD-UHFFFAOYSA-N 0.000 description 1
• KJFMBFZCATUALV-UHFFFAOYSA-N Phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 1
• 239000012346 acetyl chloride Substances 0.000 description 1
• 239000002253 acid Substances 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 230000001476 alcoholic Effects 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000005712 crystallization Effects 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 239000001257 hydrogen Substances 0.000 description 1
• 229910052739 hydrogen Inorganic materials 0.000 description 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 239000012442 inert solvent Substances 0.000 description 1
• 150000002829 nitrogen Chemical group 0.000 description 1
• 229910052757 nitrogen Inorganic materials 0.000 description 1
• 239000012299 nitrogen atmosphere Substances 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• 150000003839 salts Chemical class 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 239000012265 solid product Substances 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• 230000002048 spasmolytic Effects 0.000 description 1