IL134228A - Process for the preparation of heterocyclic compounds - Google Patents

Process for the preparation of heterocyclic compounds

Info

Publication number: IL134228A
Authority: IL; Israel
Prior art keywords: group; formula; compounds; denotes; butanol
Prior art date: 1999-01-28

Application number

IL13422800A

Other languages

English (en)

Hebrew (he)

Other versions

IL134228A0 (en

Original Assignee

Bayer 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.)

1999-01-28

Filing date

2000-01-26

Publication date

2002-11-10

2000-01-26 Application filed by Bayer Ag filed Critical Bayer Ag

2001-04-30 Publication of IL134228A0 publication Critical patent/IL134228A0/xx

2002-11-10 Publication of IL134228A publication Critical patent/IL134228A/en

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 7
150000002391 heterocyclic compounds Chemical class 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 28
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 24
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims abstract description 9
239000001301 oxygen Substances 0.000 claims abstract description 9
229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 8
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 7
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims abstract description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
239000002585 base Substances 0.000 claims abstract description 6
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims abstract description 5
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims abstract description 4
125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 4
125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 4
239000005864 Sulphur Chemical group 0.000 claims abstract description 4
150000001340 alkali metals Chemical class 0.000 claims abstract description 4
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 4
125000005842 heteroatom Chemical group 0.000 claims abstract description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
125000003118 aryl group Chemical group 0.000 claims abstract description 3
125000005843 halogen group Chemical group 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
-1 2-chloro-pyrid-5-yl Chemical group 0.000 description 7
150000001298 alcohols Chemical class 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
239000012074 organic phase Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 4
SKCNYHLTRZIINA-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)pyridine Chemical compound ClCC1=CC=C(Cl)N=C1 SKCNYHLTRZIINA-UHFFFAOYSA-N 0.000 description 3
WTUAWWLVVCGTRG-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazol-2-ylcyanamide Chemical compound N#CNC1=NCCS1 WTUAWWLVVCGTRG-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000003586 protic polar solvent Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
238000000746 purification Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000002904 solvent Substances 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000005103 alkyl silyl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910000024 caesium carbonate Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
235000011116 calcium hydroxide Nutrition 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
229910052808 lithium carbonate Inorganic materials 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229910052757 nitrogen Chemical group 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/416—2,5-Pyrrolidine-diones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pyridine Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Saccharide Compounds (AREA)
Hydrogenated Pyridines (AREA)

IL13422800A 1999-01-28 2000-01-26 Process for the preparation of heterocyclic compounds IL134228A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19904310A DE19904310A1 (de)	1999-01-28	1999-01-28	Verfahren zur Herstellung heterocyclischer Verbindungen

Publications (2)

Publication Number	Publication Date
IL134228A0 IL134228A0 (en)	2001-04-30
IL134228A true IL134228A (en)	2002-11-10

Family

ID=7896280

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL13422800A IL134228A (en)	1999-01-28	2000-01-26	Process for the preparation of heterocyclic compounds

Country Status (15)

Country	Link
US (1)	US6211379B1 (pt)
EP (1)	EP1024140B1 (pt)
JP (1)	JP2000219688A (pt)
KR (1)	KR100632521B1 (pt)
CN (1)	CN1161354C (pt)
AT (1)	ATE221530T1 (pt)
BR (1)	BR0000184B1 (pt)
CZ (1)	CZ297921B6 (pt)
DE (2)	DE19904310A1 (pt)
DK (1)	DK1024140T3 (pt)
ES (1)	ES2179798T3 (pt)
HK (1)	HK1031871A1 (pt)
HU (1)	HU225245B1 (pt)
IL (1)	IL134228A (pt)
ZA (1)	ZA200000357B (pt)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL146580A0 (en) *	1999-06-23	2002-07-25	Syngenta Participations Ag	Method of producing nitroguanidine-and nitroenamine derivatives
NZ520214A (en)	2000-01-19	2004-06-25	Bayer Ag	Process for the preparation of heterocyclic compounds
DK2751100T3 (en) *	2011-09-02	2016-01-18	Bayer Ip Gmbh	METHOD FOR PREPARING [3 - [(6-CHLOR-3-PYRIDINYL) METHYL] -2-THIAZOLIDINYLIDE] CYANAMIDE
MX2018015178A (es) *	2016-06-06	2019-04-24	Bayer Cropscience Ag	Proceso para la produccion de compuestos heterociclicos.
CN107629045A (zh) *	2017-11-10	2018-01-26	上海生农生化制品股份有限公司	一种噻虫啉的水相合成方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5933283A (ja) *	1982-08-19	1984-02-23	Fujimoto Seiyaku Kk	イソチオウレア誘導体およびその製造法
HU188852B (en) *	1983-03-16	1986-05-28	Richter Gedeon Vegyeszeti Gyar Rt,Hu	Process for producing thiazolidine derivatives active against gastric ulcer and intestinal ulcer
JPH0717621B2 (ja) *	1986-03-07	1995-03-01	日本バイエルアグロケム株式会社	新規ヘテロ環式化合物
JPH07121909B2 (ja) *	1986-09-10	1995-12-25	日本バイエルアグロケム株式会社	新規複素環式化合物及び殺虫剤

1999
- 1999-01-28 DE DE19904310A patent/DE19904310A1/de not_active Withdrawn
2000
- 2000-01-17 AT AT00100235T patent/ATE221530T1/de active
- 2000-01-17 ES ES00100235T patent/ES2179798T3/es not_active Expired - Lifetime
- 2000-01-17 DE DE50000320T patent/DE50000320D1/de not_active Expired - Lifetime
- 2000-01-17 EP EP00100235A patent/EP1024140B1/de not_active Expired - Lifetime
- 2000-01-17 DK DK00100235T patent/DK1024140T3/da active
- 2000-01-18 JP JP2000009059A patent/JP2000219688A/ja active Pending
- 2000-01-20 KR KR1020000002597A patent/KR100632521B1/ko active IP Right Grant
- 2000-01-20 US US09/488,436 patent/US6211379B1/en not_active Expired - Lifetime
- 2000-01-26 IL IL13422800A patent/IL134228A/en not_active IP Right Cessation
- 2000-01-27 ZA ZA200000357A patent/ZA200000357B/xx unknown
- 2000-01-27 BR BRPI0000184-8A patent/BR0000184B1/pt not_active IP Right Cessation
- 2000-01-27 CZ CZ20000322A patent/CZ297921B6/cs not_active IP Right Cessation
- 2000-01-28 HU HU0000366A patent/HU225245B1/hu not_active IP Right Cessation
- 2000-01-28 CN CNB001045075A patent/CN1161354C/zh not_active Expired - Lifetime
2001
- 2001-03-30 HK HK01102337A patent/HK1031871A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
CZ2000322A3 (cs)	2000-09-13
EP1024140A1 (de)	2000-08-02
HK1031871A1 (en)	2001-06-29
DE19904310A1 (de)	2000-08-03
KR20010006582A (ko)	2001-01-26
ATE221530T1 (de)	2002-08-15
DK1024140T3 (da)	2002-11-04
HU225245B1 (en)	2006-08-28
ES2179798T3 (es)	2003-02-01
DE50000320D1 (de)	2002-09-05
IL134228A0 (en)	2001-04-30
US6211379B1 (en)	2001-04-03
KR100632521B1 (ko)	2006-10-09
ZA200000357B (en)	2000-08-15
EP1024140B1 (de)	2002-07-31
HUP0000366A3 (en)	2001-12-28
JP2000219688A (ja)	2000-08-08
BR0000184A (pt)	2000-09-05
CZ297921B6 (cs)	2007-05-02
CN1269363A (zh)	2000-10-11
HU0000366D0 (en)	2000-04-28
BR0000184B1 (pt)	2010-10-19
CN1161354C (zh)	2004-08-11
HUP0000366A2 (hu)	2000-12-28

Legal Events

Date	Code	Title
2003-04-10	FF	Patent granted
2003-05-29	KB	Patent renewed
2006-03-12	KB	Patent renewed
2010-06-30	KB	Patent renewed
2014-01-30	KB	Patent renewed
2018-01-31	KB	Patent renewed
2020-08-31	EXP	Patent expired

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