IL109116A - Process for the preparation of derivatives of - 3 oxo-2,3,4-5 tetrahydro-1,2,4-triazine - Google Patents

Process for the preparation of derivatives of - 3 oxo-2,3,4-5 tetrahydro-1,2,4-triazine

Info

Publication number: IL109116A
Authority: IL; Israel
Prior art keywords: formula; compound; process according; methyl; preparation
Prior art date: 1993-03-31

Application number

IL10911694A

Other languages

English (en)

Hebrew (he)

Other versions

IL109116A0 (en

Original Assignee

Novartis Ag

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.)

1993-03-31

Filing date

1994-03-24

Publication date

1999-07-14

1994-03-24 Application filed by Novartis Ag filed Critical Novartis Ag

1994-06-24 Publication of IL109116A0 publication Critical patent/IL109116A0/xx

1999-07-14 Publication of IL109116A publication Critical patent/IL109116A/en

Links

238000000034 method Methods 0.000 title claims abstract description 35
238000002360 preparation method Methods 0.000 title claims abstract description 17
WOLFPRDERIOPJF-UHFFFAOYSA-N 4,5-dihydro-2h-1,2,4-triazin-3-one Chemical class O=C1NCC=NN1 WOLFPRDERIOPJF-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 31
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 14
230000001476 alcoholic effect Effects 0.000 claims abstract description 9
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 7
229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
229910052739 hydrogen Inorganic materials 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
-1 C^Q-alkoxy Chemical group 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
239000012429 reaction media Substances 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 2
150000003138 primary alcohols Chemical class 0.000 claims description 2
150000003333 secondary alcohols Chemical class 0.000 claims description 2
150000003509 tertiary alcohols Chemical class 0.000 claims description 2
125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract description 4
238000003797 solvolysis reaction Methods 0.000 abstract description 3
QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 abstract description 3
239000002917 insecticide Substances 0.000 abstract description 2
239000000543 intermediate Substances 0.000 abstract description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 23
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 11
VKJMPYGLTDMUPZ-UHFFFAOYSA-N 5-amino-1h-triazin-6-one Chemical compound NC1=CN=NNC1=O VKJMPYGLTDMUPZ-UHFFFAOYSA-N 0.000 description 10
150000001299 aldehydes Chemical class 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
239000000725 suspension Substances 0.000 description 9
229910052759 nickel Inorganic materials 0.000 description 8
GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 7
238000001212 derivatisation Methods 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
239000002609 medium Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 6
239000007868 Raney catalyst Substances 0.000 description 5
229910000564 Raney nickel Inorganic materials 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
238000003756 stirring Methods 0.000 description 5
FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
NYEPBMRXVGDUEZ-UHFFFAOYSA-N 5-acetyl-1h-triazin-6-one Chemical compound CC(=O)C1=CN=NNC1=O NYEPBMRXVGDUEZ-UHFFFAOYSA-N 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000012300 argon atmosphere Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
125000004641 (C1-C12) haloalkyl group Chemical group 0.000 description 1
125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 1
125000001960 7 membered carbocyclic group Chemical group 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001735 carboxylic acids Chemical group 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical class C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
230000009972 noncorrosive effect Effects 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000013341 scale-up Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

IL10911694A 1993-03-31 1994-03-24 Process for the preparation of derivatives of - 3 oxo-2,3,4-5 tetrahydro-1,2,4-triazine IL109116A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US4069193A	1993-03-31	1993-03-31

Publications (2)

Publication Number	Publication Date
IL109116A0 IL109116A0 (en)	1994-06-24
IL109116A true IL109116A (en)	1999-07-14

Family

ID=21912393

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10911694A IL109116A (en)	1993-03-31	1994-03-24	Process for the preparation of derivatives of - 3 oxo-2,3,4-5 tetrahydro-1,2,4-triazine

Country Status (20)

Country	Link
US (2)	US5384403A (de)
EP (1)	EP0618200B1 (de)
JP (1)	JP3668899B2 (de)
KR (2)	KR100306200B1 (de)
CN (2)	CN1144802C (de)
AT (1)	ATE157971T1 (de)
AU (1)	AU689459B2 (de)
BR (1)	BR9401346A (de)
CA (1)	CA2120164C (de)
CZ (2)	CZ287169B6 (de)
DE (1)	DE69405439T2 (de)
DK (1)	DK0618200T3 (de)
ES (1)	ES2110206T3 (de)
HU (1)	HU214018B (de)
IL (1)	IL109116A (de)
NZ (2)	NZ286194A (de)
PH (1)	PH30984A (de)
PL (1)	PL185421B1 (de)
SG (1)	SG46219A1 (de)
SK (1)	SK36694A3 (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9304191D0 (en) *	1993-03-02	1993-04-21	Ciba Geigy Ag	Process for the preparation of aqueous nicotinaldehyde
CO5210907A1 (es) *	1999-05-12	2002-10-30	Novartis Ag	Solvatos de pometrozina, insecticidamente activos, composiciones que contienen estos compuestos y metodos tanto para producir dichos compuestos y composiciones como para controlar plagas animales con estas composiciones
JP2006213674A (ja) *	2005-02-07	2006-08-17	Ube Ind Ltd	４−ホルミルテトラヒドロピラン化合物の製法
CN102250030B (zh) *	2010-05-17	2013-01-30	中国中化股份有限公司	一种4-氨基-6-甲基-1,2,4三嗪-3-酮制备方法
AU2012344112B9 (en)	2011-11-29	2017-02-02	Syngenta Crop Protection Ag	Insecticidal triazinone derivatives
CN112028876B (zh) *	2020-09-18	2021-04-20	河北威远生物化工有限公司	一种回收吡蚜酮的方法
CN114573561B (zh) *	2022-03-21	2023-07-18	中国农业大学	含有苄基或杂环取代的三嗪酮类化合物及其制备方法与应用

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2070861T3 (es) *	1987-10-16	1995-06-16	Ciba Geigy Ag	Compuestos antiparasitarios.
EP0391849B1 (de) *	1989-04-06	1995-04-19	Ciba-Geigy Ag	Pyridyl-methylenamino-1,2,4-triazinone
DE4011740A1 (de) *	1989-04-14	1990-10-18	Ciba Geigy Ag	1,2,4-triazinonderivate
TW199149B (de) *	1989-11-15	1993-02-01	Ciba Geigy Ag
US5324842A (en) *	1989-11-15	1994-06-28	Ciba-Geigy Corporation	Process for the preparation of aminotriazine derivatives
GB9304191D0 (en) *	1993-03-02	1993-04-21	Ciba Geigy Ag	Process for the preparation of aqueous nicotinaldehyde

1994
- 1994-02-09 US US08/194,185 patent/US5384403A/en not_active Expired - Lifetime
- 1994-02-15 PH PH47771A patent/PH30984A/en unknown
- 1994-03-21 PL PL94302711A patent/PL185421B1/pl not_active IP Right Cessation
- 1994-03-22 EP EP94810174A patent/EP0618200B1/de not_active Expired - Lifetime
- 1994-03-22 ES ES94810174T patent/ES2110206T3/es not_active Expired - Lifetime
- 1994-03-22 AT AT94810174T patent/ATE157971T1/de active
- 1994-03-22 SG SG1996001018A patent/SG46219A1/en unknown
- 1994-03-22 DK DK94810174.6T patent/DK0618200T3/da active
- 1994-03-22 DE DE69405439T patent/DE69405439T2/de not_active Expired - Lifetime
- 1994-03-24 IL IL10911694A patent/IL109116A/en not_active IP Right Cessation
- 1994-03-25 KR KR1019940006216A patent/KR100306200B1/ko not_active Expired - Fee Related
- 1994-03-28 SK SK366-94A patent/SK36694A3/sk unknown
- 1994-03-29 CA CA002120164A patent/CA2120164C/en not_active Expired - Fee Related
- 1994-03-29 CZ CZ1994739A patent/CZ287169B6/cs not_active IP Right Cessation
- 1994-03-29 CN CNB001010360A patent/CN1144802C/zh not_active Expired - Lifetime
- 1994-03-29 CN CN94103768A patent/CN1058713C/zh not_active Expired - Lifetime
- 1994-03-29 NZ NZ286194A patent/NZ286194A/en unknown
- 1994-03-29 NZ NZ260211A patent/NZ260211A/en unknown
- 1994-03-29 AU AU59140/94A patent/AU689459B2/en not_active Ceased
- 1994-03-30 JP JP08535094A patent/JP3668899B2/ja not_active Expired - Fee Related
- 1994-03-30 HU HU9400917A patent/HU214018B/hu not_active IP Right Cessation
- 1994-03-30 BR BR9401346A patent/BR9401346A/pt not_active IP Right Cessation
1995
- 1995-06-06 US US08/468,507 patent/US5514795A/en not_active Expired - Lifetime
1997
- 1997-10-07 CZ CZ19973174A patent/CZ287227B6/cs not_active IP Right Cessation
2001
- 2001-02-12 KR KR1020010006700A patent/KR100303593B1/ko not_active Expired - Fee Related

Also Published As

Publication number	Publication date
AU689459B2 (en)	1998-04-02
CN1275570A (zh)	2000-12-06
US5384403A (en)	1995-01-24
EP0618200A1 (de)	1994-10-05
PH30984A (en)	1997-12-23
HUT66867A (en)	1995-01-30
CA2120164C (en)	2004-12-21
NZ260211A (en)	1996-08-27
CN1104638A (zh)	1995-07-05
ES2110206T3 (es)	1998-02-01
DK0618200T3 (da)	1998-02-16
CZ287227B6 (cs)	2000-10-11
SG46219A1 (en)	1998-02-20
DE69405439T2 (de)	1998-02-12
DE69405439D1 (de)	1997-10-16
US5514795A (en)	1996-05-07
KR100303593B1 (ko)	2001-09-24
CN1058713C (zh)	2000-11-22
PL185421B1 (pl)	2003-05-30
AU5914094A (en)	1994-10-06
KR940021538A (ko)	1994-10-19
CZ73994A3 (en)	1994-10-19
CA2120164A1 (en)	1994-10-01
JP3668899B2 (ja)	2005-07-06
HU9400917D0 (en)	1994-06-28
BR9401346A (pt)	1994-11-01
EP0618200B1 (de)	1997-09-10
ATE157971T1 (de)	1997-09-15
CZ287169B6 (en)	2000-10-11
IL109116A0 (en)	1994-06-24
NZ286194A (en)	1996-08-27
JPH06321919A (ja)	1994-11-22
CN1144802C (zh)	2004-04-07
HU214018B (en)	1997-12-29
SK36694A3 (en)	1995-02-08
KR100306200B1 (ko)	2001-12-28

Legal Events

Date	Code	Title
1999-11-30	FF	Patent granted
2000-06-01	KB	Patent renewed
2000-08-13	KB	Patent renewed
2004-02-19	HP	Change in proprietorship
2004-06-01	KB	Patent renewed
2008-04-13	KB	Patent renewed
2012-03-29	KB	Patent renewed
2014-11-30	EXP	Patent expired

Publication	Publication Date	Title
IL109116A (en)	1999-07-14	Process for the preparation of derivatives of - 3 oxo-2,3,4-5 tetrahydro-1,2,4-triazine
CA2493275C (en)	2007-01-23	Processes for the preparation of triazinone derivatives
NZ238526A (en)	1992-05-26	Preparation of indapamide
HU225940B1 (en)	2008-01-28	Processes for preparing pesticidal intermediates
EP0788488A1 (de)	1997-08-13	Verbessertes verfahren zur herstellung von 5-aminotetrazol
IL108767A (en)	1999-03-12	Process for Preparation 6 - Alkyl - 4 -) Pyridine - 3 - Il - Methylamino (- 4, 5 - Dihydro - 1, 2, 4 - Triazine - H) 23 (- On
US4327033A (en)	1982-04-27	Process for the production of methomyl oxime
US5274100A (en)	1993-12-28	Process for the preparation of (3-fluoropyridin-2-yloxy)phenoxypropionic acids
NO820073L (no)	1982-07-14	Fremgangsmaate for fremstilling av 4-aminobutyramider
PL185411B1 (pl)	2003-05-30	Sposób wytwarzania pochodnych pirydyloaminotriazyny
HU206320B (en)	1992-10-28	Process for producing 8-aza-spiro/4,5/decane-7,9-dione