JPS6363651A - ニトロンの製造法 - Google Patents

ニトロンの製造法

Info

Publication number: JPS6363651A
Authority: JP; Japan
Prior art keywords: group; producing; nitrone; methanol; formula
Prior art date: 1986-09-05
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

Application number

JP61208062A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0244830B2 (es

Inventor

Shunichi Murahashi

俊一村橋

Tatsuki Shioda

塩田　辰樹

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Osaka University NUC

Original Assignee

Osaka University NUC

Priority date (The priority date 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 date listed.)

1986-09-05

Filing date

1986-09-05

Publication date

1988-03-22

1986-09-05 Application filed by Osaka University NUC filed Critical Osaka University NUC

1986-09-05 Priority to JP61208062A priority Critical patent/JPS6363651A/ja

1988-03-22 Publication of JPS6363651A publication Critical patent/JPS6363651A/ja

1990-10-05 Publication of JPH0244830B2 publication Critical patent/JPH0244830B2/ja

Status Granted legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 10
CWGBFIRHYJNILV-UHFFFAOYSA-N (1,4-diphenyl-1,2,4-triazol-4-ium-3-yl)-phenylazanide Chemical compound C=1C=CC=CC=1[N-]C1=NN(C=2C=CC=CC=2)C=[N+]1C1=CC=CC=C1 CWGBFIRHYJNILV-UHFFFAOYSA-N 0.000 title abstract 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 57
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 22
238000006243 chemical reaction Methods 0.000 claims abstract description 16
229940065287 selenium compound Drugs 0.000 claims abstract description 9
150000003343 selenium compounds Chemical class 0.000 claims abstract description 9
150000002978 peroxides Chemical class 0.000 claims abstract description 7
150000001336 alkenes Chemical class 0.000 claims abstract description 5
239000003960 organic solvent Substances 0.000 claims abstract description 5
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 4
125000002723 alicyclic group Chemical group 0.000 claims abstract 2
125000001931 aliphatic group Chemical group 0.000 claims abstract 2
125000000623 heterocyclic group Chemical group 0.000 claims abstract 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 22
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
-1 alkali metal salts Chemical class 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
229940082569 selenite Drugs 0.000 claims description 3
MCAHWIHFGHIESP-UHFFFAOYSA-L selenite(2-) Chemical class [O-][Se]([O-])=O MCAHWIHFGHIESP-UHFFFAOYSA-L 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
150000000660 7-membered heterocyclic compounds Chemical class 0.000 claims description 2
150000001298 alcohols Chemical class 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
239000004215 Carbon black (E152) Substances 0.000 claims 1
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
229930195733 hydrocarbon Natural products 0.000 claims 1
150000002430 hydrocarbons Chemical class 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 abstract description 28
239000003054 catalyst Substances 0.000 abstract description 9
150000001412 amines Chemical class 0.000 abstract description 4
239000003905 agrochemical Substances 0.000 abstract description 3
239000012847 fine chemical Substances 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 2
150000004945 aromatic hydrocarbons Chemical group 0.000 abstract 1
125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
MCAHWIHFGHIESP-UHFFFAOYSA-N selenous acid Chemical compound O[Se](O)=O MCAHWIHFGHIESP-UHFFFAOYSA-N 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
239000000203 mixture Substances 0.000 description 20
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 19
238000000034 method Methods 0.000 description 14
238000001816 cooling Methods 0.000 description 13
238000004440 column chromatography Methods 0.000 description 12
239000003480 eluent Substances 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
239000012300 argon atmosphere Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 9
150000001875 compounds Chemical class 0.000 description 8
150000003512 tertiary amines Chemical class 0.000 description 8
239000007858 starting material Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 4
239000005457 ice water Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
230000001747 exhibiting effect Effects 0.000 description 3
AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine group Chemical group NO AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
230000000975 bioactive effect Effects 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
239000002243 precursor Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
XXRIRANJUFOEDA-AATRIKPKSA-N (e)-n-tert-butylbut-2-en-1-amine Chemical compound C\C=C\CNC(C)(C)C XXRIRANJUFOEDA-AATRIKPKSA-N 0.000 description 1
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 1
IUXYVKZUDNLISR-UHFFFAOYSA-N 2-(tert-butylamino)ethanol Chemical compound CC(C)(C)NCCO IUXYVKZUDNLISR-UHFFFAOYSA-N 0.000 description 1
NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical compound CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 description 1
NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
BPSLFSXCUJYFIR-UHFFFAOYSA-N 7-methoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1CNCC2=CC(OC)=CC=C21 BPSLFSXCUJYFIR-UHFFFAOYSA-N 0.000 description 1
ZFDIRQKJPRINOQ-HWKANZROSA-N Ethyl crotonate Chemical compound CCOC(=O)\C=C\C ZFDIRQKJPRINOQ-HWKANZROSA-N 0.000 description 1
125000000815 N-oxide group Chemical group 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910000474 mercury oxide Inorganic materials 0.000 description 1
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
BLWYXBNNBYXPPL-UHFFFAOYSA-N methyl pyrrolidine-2-carboxylate Chemical compound COC(=O)C1CCCN1 BLWYXBNNBYXPPL-UHFFFAOYSA-N 0.000 description 1
PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
VACPZDQXUAOTFR-UHFFFAOYSA-N n-tert-butylbutan-1-amine Chemical compound CCCCNC(C)(C)C VACPZDQXUAOTFR-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
YAVXLTMRALFZIS-UHFFFAOYSA-N piperidine-2-carbonitrile Chemical compound N#CC1CCCCN1 YAVXLTMRALFZIS-UHFFFAOYSA-N 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
150000003658 tungsten compounds Chemical class 0.000 description 1

Landscapes

Other In-Based Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Pyrrole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP61208062A 1986-09-05 1986-09-05 ニトロンの製造法 Granted JPS6363651A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP61208062A JPS6363651A (ja)	1986-09-05	1986-09-05	ニトロンの製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP61208062A JPS6363651A (ja)	1986-09-05	1986-09-05	ニトロンの製造法

Publications (2)

Publication Number	Publication Date
JPS6363651A true JPS6363651A (ja)	1988-03-22
JPH0244830B2 JPH0244830B2 (es)	1990-10-05

Family

ID=16550011

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP61208062A Granted JPS6363651A (ja)	1986-09-05	1986-09-05	ニトロンの製造法

Country Status (1)

Country	Link
JP (1)	JPS6363651A (es)

1986
- 1986-09-05 JP JP61208062A patent/JPS6363651A/ja active Granted

Also Published As

Publication number	Publication date
JPH0244830B2 (es)	1990-10-05

Legal Events

Date	Code	Title	Description
2006-09-05	EXPY	Cancellation because of completion of term

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