SK142894A3 - Method of preparing 5-dichloracetyl-3,3,6-trimethyl-9-oxo- -1,5-diazabicyclo £4,3,0| nonane - Google Patents

Method of preparing 5-dichloracetyl-3,3,6-trimethyl-9-oxo- -1,5-diazabicyclo £4,3,0| nonane Download PDF

Info

Publication number: SK142894A3
Authority: SK; Slovakia
Prior art keywords: reaction; formula; nonane; trimethyl; oxo
Prior art date: 1992-05-29

Application number

SK1428-94A

Other languages

English (en)

Slovak (sk)

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

1993-05-18

Publication date

1995-06-07

1993-05-18 Application filed by Basf Ag filed Critical Basf Ag

1995-06-07 Publication of SK142894A3 publication Critical patent/SK142894A3/sk

Links

238000000034 method Methods 0.000 title claims description 15
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 title 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 29
238000006243 chemical reaction Methods 0.000 claims abstract description 24
229910001868 water Inorganic materials 0.000 claims abstract description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 claims abstract description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 13
239000003960 organic solvent Substances 0.000 claims abstract description 10
239000002904 solvent Substances 0.000 claims abstract description 8
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 6
239000008346 aqueous phase Substances 0.000 claims abstract description 6
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 claims abstract description 5
238000004519 manufacturing process Methods 0.000 claims abstract description 3
239000012071 phase Substances 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 11
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 5
DDHUNHGZUHZNKB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diamine Chemical compound NCC(C)(C)CN DDHUNHGZUHZNKB-UHFFFAOYSA-N 0.000 claims description 2
150000001555 benzenes Chemical class 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000007790 solid phase Substances 0.000 claims description 2
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 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
150000001875 compounds Chemical class 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 7
239000007787 solid Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
XDIAMRVROCPPBK-UHFFFAOYSA-N 2,2-dimethylpropan-1-amine Chemical compound CC(C)(C)CN XDIAMRVROCPPBK-UHFFFAOYSA-N 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
239000002585 base Substances 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
230000002051 biphasic effect Effects 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
239000007858 starting material Substances 0.000 description 3
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
150000003738 xylenes Chemical class 0.000 description 2
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
150000008061 acetanilides Chemical class 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
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
239000012455 biphasic mixture Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000001816 cooling 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
238000002955 isolation Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification 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
230000007704 transition Effects 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003799 water insoluble solvent Substances 0.000 description 1
239000003021 water soluble solvent Substances 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)

SK1428-94A 1992-05-29 1993-05-18 Method of preparing 5-dichloracetyl-3,3,6-trimethyl-9-oxo- -1,5-diazabicyclo £4,3,0| nonane SK142894A3 (en)

Applications Claiming Priority (2)

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
PCT/EP1993/001234 WO1993024489A1 (de)	1992-05-29	1993-05-18	Verfahren zur herstellung von 5-dichloracetyl-3,3,6-trimethyl-9-oxo-1,5-diazabycyclo[4,3,0]nonan

Publications (1)

Publication Number	Publication Date
SK142894A3 true SK142894A3 (en)	1995-06-07

Family

ID=6460024

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1428-94A SK142894A3 (en)	1992-05-29	1993-05-18	Method of preparing 5-dichloracetyl-3,3,6-trimethyl-9-oxo- -1,5-diazabicyclo £4,3,0\| nonane

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

Family Cites Families (6)

* 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
DE2948535A1 (de) *	1979-12-03	1981-06-25	Basf Ag, 6700 Ludwigshafen	Dichloracetamide, herbizide mittel, die acetanilide als herbizide wirkstoffe und diese dichloracetamide als antagonistische mittel enthalten, sowie ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses
EP0190105A3 (de) *	1985-01-31	1988-10-26	Ciba-Geigy Ag	Herbizides Mittel
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
DE3600903A1 (de) *	1986-01-15	1987-07-16	Basf Ag	Optisch aktive diazabicycloalkanderivate, ein verfahren zu ihrer herstellung und ihre verwendung zum schutz von kulturpflanzen vor der phytotoxischen wirkung von herbiziden
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

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
LT3016B (lt)	1994-08-25
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
HU213833B (en)	1997-10-28
HU9403409D0 (en)	1995-03-28
DE59303673D1 (de)	1996-10-10

Publication	Publication Date	Title
DK170335B1 (da)	1995-08-07	Fremgangsmåde til fremstilling af 5-cyano-10-nitro-5H-dibenz(b,f)azepin
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
EP0609179B1 (de)	1996-07-17	Herstellung aromatischer Nitrile
SK142894A3 (en)	1995-06-07	Method of preparing 5-dichloracetyl-3,3,6-trimethyl-9-oxo- -1,5-diazabicyclo £4,3,0\| nonane
US4020104A (en)	1977-04-26	Process for isomerizing cis,cis- and cis,trans-isomers of di-(p-aminocyclohexyl)methane to the corresponding trans,trans-isomer
US4997967A (en)	1991-03-05	Process for the preparation of isothiocyanates
KR20070039948A (ko)	2007-04-13	2-아미노-5-요오도 안식향산의 제조 방법
US3822311A (en)	1974-07-02	Process for the production of 2,5-dichloro-3-nitro-benzoic acid
US4427600A (en)	1984-01-24	Preparation of 1-alkyl-2-chloro-5-nitrobenzene-4-sulfonic acids
US4058563A (en)	1977-11-15	Novel schiff bases
US5405998A (en)	1995-04-11	Process for the manufacture of cycloalkyl and haloalkyl o-aminophenyl ketones
CA1106854A (en)	1981-08-11	Process for the preparation of para-nitroso- diphenylhydroxylamines
KR20010102956A (ko)	2001-11-17	폴리할로겐화 파라트리플루오로메틸아닐린의 제조 방법
US4774358A (en)	1988-09-27	Cyclopropylamines containing trifluoromethyl groups
EP0872473A2 (en)	1998-10-21	Process for the preparation of chloroketoamines using carbamates
US4454344A (en)	1984-06-12	Method for the resolution of racemic 2-(p-difluoromethoxyphenyl)-3-methylbutyric acid
US3452043A (en)	1969-06-24	Production of 1-n,n-dimethylcarbamoyl-5 - methyl - 3 - n,n-dimethyl-carbamoyloxy-pyrazole
US4010160A (en)	1977-03-01	Process for the manufacture of 1,3-bis-(β-ethylhexyl)-5-amino-5-methyl-hexahydropyrimidine
US3078317A (en)	1963-02-19	Mononitration of 1, 3, 5-trialkylbenzene
EP0101570B1 (en)	1988-01-27	Method for the resolution of racemic 2-cp-difluoromethoxy phenyl)-3-methylbutyric acid
EP0102652B1 (de)	1986-01-08	Verfahren zur Reindarstellung von 2-Chlor-6-alkoxy-3-nitropyridinen
US4034050A (en)	1977-07-05	Preparation of 5-methyl-2-nitrophenol
PL86547B1 (cs)	1976-06-30
FI56672C (fi)	1980-03-10	Nytt foerfarande foer framstaellning av 2-amino-benzaminer