BE554776A - - Google Patents

Info

Publication number

BE554776A

BE554776A BE554776DA BE554776A BE 554776 A BE554776 A BE 554776A BE 554776D A BE554776D A BE 554776DA BE 554776 A BE554776 A BE 554776A

Authority

BE

Belgium

Prior art keywords

alkyl

alkyl group

acid

methyl

hydrogenated

Prior art date

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• 125000000217 alkyl group Chemical group 0.000 claims description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
• 239000002253 acid Substances 0.000 claims description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 150000001408 amides Chemical class 0.000 claims description 4
• 150000002148 esters Chemical class 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 239000011777 magnesium Substances 0.000 claims description 3
• 229910052757 nitrogen Inorganic materials 0.000 claims description 3
• 230000029936 alkylation Effects 0.000 claims description 2
• 238000005804 alkylation reaction Methods 0.000 claims description 2
• 239000007795 chemical reaction product Substances 0.000 claims description 2
• 125000000623 heterocyclic group Chemical group 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 claims description 2
• 125000001424 substituent group Chemical group 0.000 claims description 2
• 150000004792 aryl magnesium halides Chemical class 0.000 claims 1
• 150000004820 halides Chemical class 0.000 claims 1
• 238000005984 hydrogenation reaction Methods 0.000 claims 1
• 238000000034 method Methods 0.000 claims 1
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
• 238000006467 substitution reaction Methods 0.000 claims 1
• UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 4
• PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 239000000047 product Substances 0.000 description 3
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
• -1 aniline-magnesium halide Chemical class 0.000 description 2
• 150000001555 benzenes Chemical group 0.000 description 2
• 239000007789 gas Substances 0.000 description 2
• 229910052749 magnesium Inorganic materials 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• FLAKGKCBSLMHQU-UHFFFAOYSA-N CC[Mg] Chemical compound CC[Mg] FLAKGKCBSLMHQU-UHFFFAOYSA-N 0.000 description 1
• CZXDFVZOBRBANZ-UHFFFAOYSA-N NC1=CC=CC=C1.[Mg] Chemical compound NC1=CC=CC=C1.[Mg] CZXDFVZOBRBANZ-UHFFFAOYSA-N 0.000 description 1
• XQMUEFDDYYIRPT-UHFFFAOYSA-L [Br-].[Mg+2].C(C)C1=C(N)C=CC=C1.[Br-] Chemical compound [Br-].[Mg+2].C(C)C1=C(N)C=CC=C1.[Br-] XQMUEFDDYYIRPT-UHFFFAOYSA-L 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 150000004791 alkyl magnesium halides Chemical class 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 150000001448 anilines Chemical class 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 125000004429 atom Chemical group 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
• 125000004432 carbon atom Chemical group C* 0.000 description 1
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
• 125000004494 ethyl ester group Chemical group 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 239000001257 hydrogen Substances 0.000 description 1
• 229910052739 hydrogen Inorganic materials 0.000 description 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
• 239000012535 impurity Substances 0.000 description 1
• 239000003589 local anesthetic agent Substances 0.000 description 1
• ONXRNTKLIOTLCJ-UHFFFAOYSA-L magnesium 2,6-dimethylaniline dibromide Chemical compound [Br-].[Mg+2].CC1=C(N)C(=CC=C1)C.[Br-] ONXRNTKLIOTLCJ-UHFFFAOYSA-L 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 229940102396 methyl bromide Drugs 0.000 description 1
• GZUXJHMPEANEGY-UHFFFAOYSA-N methyl bromide Substances BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 235000011121 sodium hydroxide Nutrition 0.000 description 1
• 239000000243 solution Substances 0.000 description 1