JP2010516644A5 - - Google Patents

Info

Publication number

JP2010516644A5

JP2010516644A5 JP2009545869A JP2009545869A JP2010516644A5 JP 2010516644 A5 JP2010516644 A5 JP 2010516644A5 JP 2009545869 A JP2009545869 A JP 2009545869A JP 2009545869 A JP2009545869 A JP 2009545869A JP 2010516644 A5 JP2010516644 A5 JP 2010516644A5

Authority

JP

Japan

Prior art keywords

solvent

acetamidine

mixture

salt

compounds

Prior art date

2008-01-17

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.)

Granted

Links

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• 239000002904 solvent Substances 0.000 claims description 14
• 125000000217 alkyl group Chemical group 0.000 claims description 8
• 239000000203 mixture Substances 0.000 claims description 8
• 239000002841 Lewis acid Substances 0.000 claims description 7
• 150000001875 compounds Chemical class 0.000 claims description 7
• 150000007517 lewis acids Chemical class 0.000 claims description 7
• 125000003118 aryl group Chemical group 0.000 claims description 6
• 125000004122 cyclic group Chemical group 0.000 claims description 6
• OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical class CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 5
• 150000003839 salts Chemical class 0.000 claims description 5
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
• 125000001931 aliphatic group Chemical group 0.000 claims description 4
• 230000035484 reaction time Effects 0.000 claims description 4
• IATHTLTVQXMDPC-UHFFFAOYSA-N 2-methyl-3-oxopropanenitrile Chemical class O=CC(C)C#N IATHTLTVQXMDPC-UHFFFAOYSA-N 0.000 claims description 2
• 239000003570 air Substances 0.000 claims description 2
• 229910052786 argon Inorganic materials 0.000 claims description 2
• 125000001072 heteroaryl group Chemical group 0.000 claims description 2
• 239000001257 hydrogen Substances 0.000 claims description 2
• 229910052739 hydrogen Inorganic materials 0.000 claims description 2
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 229910052757 nitrogen Inorganic materials 0.000 claims description 2
• 238000003756 stirring Methods 0.000 claims description 2
• 125000003107 substituted aryl group Chemical group 0.000 claims description 2
• 238000000034 method Methods 0.000 claims 24
• FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical group CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims 10
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 6
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
• 229910021591 Copper(I) chloride Inorganic materials 0.000 claims 2
• 150000004649 carbonic acid derivatives Chemical class 0.000 claims 2
• OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims 2
• WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical group Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 claims 2
• 150000002576 ketones Chemical class 0.000 claims 2
• 150000003512 tertiary amines Chemical class 0.000 claims 2
• 229910052723 transition metal Inorganic materials 0.000 claims 2
• 150000003624 transition metals Chemical class 0.000 claims 2
• VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 claims 1
• 239000004912 1,5-cyclooctadiene Substances 0.000 claims 1
• ZOZNCAMOIPYYIK-UHFFFAOYSA-N 1-aminoethylideneazanium;acetate Chemical compound CC(N)=N.CC(O)=O ZOZNCAMOIPYYIK-UHFFFAOYSA-N 0.000 claims 1
• VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims 1
• CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims 1
• PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims 1
• 239000002253 acid Substances 0.000 claims 1
• 150000001298 alcohols Chemical class 0.000 claims 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
• 150000001342 alkaline earth metals Chemical class 0.000 claims 1
• 150000001408 amides Chemical class 0.000 claims 1
• 150000001491 aromatic compounds Chemical group 0.000 claims 1
• 239000010953 base metal Substances 0.000 claims 1
• XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical class [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 claims 1
• 238000010276 construction Methods 0.000 claims 1
• 150000002148 esters Chemical class 0.000 claims 1
• CWJKVUQGXKYWTR-UHFFFAOYSA-N ethanimidamide;hydrobromide Chemical compound Br.CC(N)=N CWJKVUQGXKYWTR-UHFFFAOYSA-N 0.000 claims 1
• 150000002170 ethers Chemical class 0.000 claims 1
• 229930195733 hydrocarbon Natural products 0.000 claims 1
• 150000002430 hydrocarbons Chemical group 0.000 claims 1
• -1 lanthanide salts Chemical class 0.000 claims 1
• 229910052747 lanthanoid Inorganic materials 0.000 claims 1
• 150000002825 nitriles Chemical class 0.000 claims 1
• 125000000075 primary alcohol group Chemical group 0.000 claims 1
• 230000001681 protective effect Effects 0.000 claims 1
• YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical class [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 claims 1
• 239000011701 zinc Substances 0.000 claims 1
• 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1