LT3016B - 5-dichloracetil-3,3,6-trimetil-9-okso-i,5-diazabiciklo £4,3,0| nonano gavimo budas - Google Patents

5-dichloracetil-3,3,6-trimetil-9-okso-i,5-diazabiciklo £4,3,0| nonano gavimo budas Download PDF

Info

Publication number: LT3016B
Authority: LT; Lithuania
Prior art keywords: trimethyl; oxo; nonane; water; dichloroacetyl
Prior art date: 1992-05-29

Application number

LTIP575A

Other languages

English (en)

Lithuanian (lt)

Inventor

Gernot Reissenweber

Winfried Richarz

Knut Koob

Original Assignee

Basf 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.)

1992-05-29

Filing date

1993-05-28

Publication date

1994-08-25

1993-05-28 Application filed by Basf Ag filed Critical Basf Ag

1994-04-25 Publication of LTIP575A publication Critical patent/LTIP575A/lt

1994-08-25 Publication of LT3016B publication Critical patent/LT3016B/lt

Links

238000000034 method Methods 0.000 title claims description 8
MHULQDZDXMHODA-UHFFFAOYSA-N 1-(2,2-dichloroacetyl)-3,3,8a-trimethyl-2,4,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-6-one Chemical compound C1C(C)(C)CN(C(=O)C(Cl)Cl)C2(C)N1C(=O)CC2 MHULQDZDXMHODA-UHFFFAOYSA-N 0.000 title abstract description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
229910001868 water Inorganic materials 0.000 claims abstract description 18
238000006243 chemical reaction Methods 0.000 claims abstract description 15
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 claims abstract description 15
239000003960 organic solvent Substances 0.000 claims abstract description 10
QNQGPTNLHJCUJS-UHFFFAOYSA-N 3,3,8a-trimethyl-2,4,7,8-tetrahydro-1h-pyrrolo[1,2-a]pyrimidin-6-one Chemical compound C1C(C)(C)CNC2(C)N1C(=O)CC2 QNQGPTNLHJCUJS-UHFFFAOYSA-N 0.000 claims abstract description 9
239000002904 solvent Substances 0.000 claims abstract description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 7
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 6
239000008346 aqueous phase Substances 0.000 claims abstract description 5
238000004519 manufacturing process Methods 0.000 claims abstract description 3
JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims description 10
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 7
239000012265 solid product Substances 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims description 3
230000002051 biphasic effect Effects 0.000 claims description 3
239000000203 mixture Substances 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 16
239000012071 phase Substances 0.000 abstract description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 10
XDIAMRVROCPPBK-UHFFFAOYSA-N 2,2-dimethylpropan-1-amine Chemical compound CC(C)(C)CN XDIAMRVROCPPBK-UHFFFAOYSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
239000000047 product Substances 0.000 description 5
239000000243 solution Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
238000000926 separation method Methods 0.000 description 2
150000003738 xylenes Chemical class 0.000 description 2
238000003436 Schotten-Baumann reaction Methods 0.000 description 1
229960001413 acetanilide Drugs 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
239000000729 antidote Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
-1 benzene Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000012455 biphasic mixture Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
244000038559 crop plants Species 0.000 description 1
230000007423 decrease Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
229940040102 levulinic acid Drugs 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000011403 purification operation Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Cephalosporin Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

LTIP575A 1992-05-29 1993-05-28 5-dichloracetil-3,3,6-trimetil-9-okso-i,5-diazabiciklo £4,3,0| nonano gavimo budas LT3016B (lt)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4217846A DE4217846C1 (de)	1992-05-29	1992-05-29	Verfahren zur Herstellung von 5-Dichloracetyl-3,3,6-trimethyl-9-oxo-1,5-diazabicyclo[4,3,0]nonan

Publications (2)

Publication Number	Publication Date
LTIP575A LTIP575A (lt)	1994-04-25
LT3016B true LT3016B (lt)	1994-08-25

Family

ID=6460024

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LTIP575A LT3016B (lt)	1992-05-29	1993-05-28	5-dichloracetil-3,3,6-trimetil-9-okso-i,5-diazabiciklo £4,3,0\| nonano gavimo budas

Country Status (15)

Country	Link
US (1)	US5677452A (cs)
EP (1)	EP0642511B1 (cs)
AT (1)	ATE142210T1 (cs)
AU (1)	AU4313293A (cs)
CA (1)	CA2136872C (cs)
CZ (1)	CZ276094A3 (cs)
DE (2)	DE4217846C1 (cs)
ES (1)	ES2091007T3 (cs)
HU (1)	HU213833B (cs)
LT (1)	LT3016B (cs)
LV (1)	LV11036B (cs)
PL (1)	PL173088B1 (cs)
RU (1)	RU94046203A (cs)
SK (1)	SK142894A3 (cs)
WO (1)	WO1993024489A1 (cs)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6476046B1 (en)	2000-12-04	2002-11-05	Sepracor, Inc.	Diazabicyclo[4.3.0]nonanes, and methods of use thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1802468A1 (de)	1968-10-11	1970-05-21	Bayer Ag	Diazabicycloalkane
EP0031042A1 (de)	1979-12-03	1981-07-01	BASF Aktiengesellschaft	N-Dichloracetyldiazabicycloderivate,Verfahren zu ihrer Herstellung,herbizide Mittel,die Acetanilide als herbizide Wirkstoffe und diese N-Dichloroacetyldiazaantagonistische Mittel enthalten, sowie ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
EP0190105A2 (de)	1985-01-31	1986-08-06	Ciba-Geigy Ag	Herbizides Mittel
EP0229649A2 (de)	1986-01-15	1987-07-22	BASF Aktiengesellschaft	Optisch aktive Diazabicycloalkanderivate und ihre Verwendung zum Schutz von Kulturpflanzen vor der phytotoxischen Wirkung von Herbiziden

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4995899A (en) *	1986-01-15	1991-02-26	Basf Aktiengesellschaft	Optically active diazabicycloalkane derivatives and their use for protecting crops from the phytotoxic effect of herbicides
GB8916395D0 (en) *	1989-07-18	1989-09-06	Zambeletti Spa L	Pharmaceuticals

1992
- 1992-05-29 DE DE4217846A patent/DE4217846C1/de not_active Expired - Lifetime
1993
- 1993-05-18 CZ CZ942760A patent/CZ276094A3/cs unknown
- 1993-05-18 SK SK1428-94A patent/SK142894A3/sk unknown
- 1993-05-18 ES ES93912713T patent/ES2091007T3/es not_active Expired - Lifetime
- 1993-05-18 PL PL93306379A patent/PL173088B1/pl not_active IP Right Cessation
- 1993-05-18 RU RU94046203/04A patent/RU94046203A/ru unknown
- 1993-05-18 WO PCT/EP1993/001234 patent/WO1993024489A1/de not_active Ceased
- 1993-05-18 DE DE59303673T patent/DE59303673D1/de not_active Expired - Lifetime
- 1993-05-18 AU AU43132/93A patent/AU4313293A/en not_active Abandoned
- 1993-05-18 HU HU9403409A patent/HU213833B/hu not_active IP Right Cessation
- 1993-05-18 EP EP93912713A patent/EP0642511B1/de not_active Expired - Lifetime
- 1993-05-18 CA CA002136872A patent/CA2136872C/en not_active Expired - Fee Related
- 1993-05-18 AT AT93912713T patent/ATE142210T1/de not_active IP Right Cessation
- 1993-05-27 LV LVP-93-432A patent/LV11036B/lv unknown
- 1993-05-28 LT LTIP575A patent/LT3016B/lt not_active IP Right Cessation
1996
- 1996-10-24 US US08/736,438 patent/US5677452A/en not_active Expired - Lifetime

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1802468A1 (de)	1968-10-11	1970-05-21	Bayer Ag	Diazabicycloalkane
EP0031042A1 (de)	1979-12-03	1981-07-01	BASF Aktiengesellschaft	N-Dichloracetyldiazabicycloderivate,Verfahren zu ihrer Herstellung,herbizide Mittel,die Acetanilide als herbizide Wirkstoffe und diese N-Dichloroacetyldiazaantagonistische Mittel enthalten, sowie ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
EP0190105A2 (de)	1985-01-31	1986-08-06	Ciba-Geigy Ag	Herbizides Mittel
EP0229649A2 (de)	1986-01-15	1987-07-22	BASF Aktiengesellschaft	Optisch aktive Diazabicycloalkanderivate und ihre Verwendung zum Schutz von Kulturpflanzen vor der phytotoxischen Wirkung von Herbiziden

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HOUBEN-WEIL: "Methoden der organischen Chemie"

Also Published As

Publication number	Publication date
RU94046203A (ru)	1996-09-27
WO1993024489A1 (de)	1993-12-09
DE4217846C1 (de)	1993-12-23
LV11036B (en)	1996-06-20
PL173088B1 (pl)	1998-01-30
ATE142210T1 (de)	1996-09-15
AU4313293A (en)	1993-12-30
ES2091007T3 (es)	1996-10-16
CZ276094A3 (en)	1995-02-15
US5677452A (en)	1997-10-14
LV11036A (lv)	1996-02-20
CA2136872C (en)	2004-01-20
EP0642511B1 (de)	1996-09-04
HUT69060A (en)	1995-08-28
CA2136872A1 (en)	1993-05-18
LTIP575A (lt)	1994-04-25
EP0642511A1 (de)	1995-03-15
SK142894A3 (en)	1995-06-07
HU213833B (en)	1997-10-28
HU9403409D0 (en)	1995-03-28
DE59303673D1 (de)	1996-10-10

Legal Events

Date	Code	Title	Description
2000-01-25	MM9A	Lapsed patents	Effective date: 19990528

Publication	Publication Date	Title
CZ290293A3 (en)	1994-07-13	Process for preparing 2-alkyl-6-methyl-n-(1°-methoxy-2°-propyl)-aniline and process for preparing chloroacetanilides thereof
JP2008516005A (ja)	2008-05-15	レトロゾールの改良された調製方法
US6214998B1 (en)	2001-04-10	Process for preparing 2-chloro-5-chloromethylthiazole
LT3016B (lt)	1994-08-25	5-dichloracetil-3,3,6-trimetil-9-okso-i,5-diazabiciklo £4,3,0\| nonano gavimo budas
US4434292A (en)	1984-02-28	Process for the preparation of pyrazole
US20020087008A1 (en)	2002-07-04	Process for preparing 2-chloro-5-chloromethylthiazole
KR100244880B1 (ko)	2000-03-02	2-클로로-5-알킬아미노메틸-피리딘의제조방법
US3822311A (en)	1974-07-02	Process for the production of 2,5-dichloro-3-nitro-benzoic acid
US5405998A (en)	1995-04-11	Process for the manufacture of cycloalkyl and haloalkyl o-aminophenyl ketones
US4607108A (en)	1986-08-19	Process for the preparation of 3-isomers of 1-cyclohexyl-2-(1,2,4-triazol-1-yl)-1-penten-3-one derivatives
US3452043A (en)	1969-06-24	Production of 1-n,n-dimethylcarbamoyl-5 - methyl - 3 - n,n-dimethyl-carbamoyloxy-pyrazole
JP2002503240A (ja)	2002-01-29	カルボニルジイミダゾール、そのエステル誘導体およびその製造方法
CA1052383A (en)	1979-04-10	Process for the production of 1,2,4-triazole derivatives
KR100452077B1 (ko)	2004-11-16	방향족니트릴의제조방법
US4010160A (en)	1977-03-01	Process for the manufacture of 1,3-bis-(β-ethylhexyl)-5-amino-5-methyl-hexahydropyrimidine
US6252069B1 (en)	2001-06-26	Method for the production of 3-isopropyl-1H-2, 1,3-benzothiadiazine-4 (3H)-one-2,2-dioxide
US3479369A (en)	1969-11-18	Alkyl- or aryl-4-antipyrylmonosulfides and method for preparing same
JP2000517325A (ja)	2000-12-26	アミジンの製造方法
JPS60172963A (ja)	1985-09-06	２，２，６，６−テトラメチル−４−オキソピペリジンの製造方法
JP4739695B2 (ja)	2011-08-03	５−アミノ―１―置換―１，２，４―トリアゾールの製造方法、及び該製造方法で得られるトリアゾール誘導体
JP2002155058A (ja)	2002-05-28	１位置換ヒダントイン類の製造方法
US4503238A (en)	1985-03-05	Preparation of dihydro-4,4-dimethylfuran-2,3-dione
Harfenist et al.	1958	The Preparation and Stereochemistry of Some Cinnamonitriles, Some Cinnamamidines and Related Compounds
HU193454B (en)	1987-10-28	Process for producing 3-phenyl-butyraldehyde derivatives
JPS5829786B2 (ja)	1983-06-24	アルフア − オキソチオジメチルアミドセイホウ