DD237503A5 - Verfahren zur herstellung halogenierten aroylessigestern - Google Patents

Verfahren zur herstellung halogenierten aroylessigestern Download PDF

Info

Publication number: DD237503A5
Authority: DD; German Democratic Republic
Prior art keywords: ketone; chloride; methylene chloride; halogen; dichloroethylene
Prior art date: 1984-07-18

Application number

DD85278635A

Other languages

German (de)

English (en)

Inventor

Klaus Grohe

Original Assignee

��@��k��

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.)

1984-07-18

Filing date

1985-07-16

Publication date

1986-07-16

1985-07-16 Application filed by ��@��k�� filed Critical ��@��k��

1986-07-16 Publication of DD237503A5 publication Critical patent/DD237503A5/de

Links

150000002148 esters Chemical class 0.000 title abstract 2
238000004519 manufacturing process Methods 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 16
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims abstract description 9
150000002367 halogens Chemical class 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
238000002360 preparation method Methods 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
239000011737 fluorine Substances 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract description 14
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract description 11
239000011260 aqueous acid Substances 0.000 abstract description 3
239000000543 intermediate Substances 0.000 abstract description 3
230000000844 anti-bacterial effect Effects 0.000 abstract description 2
CYJDINODOIMUEB-UHFFFAOYSA-N 1,1,1,5,5,5-hexachloropentan-3-one Chemical compound ClC(Cl)(Cl)CC(=O)CC(Cl)(Cl)Cl CYJDINODOIMUEB-UHFFFAOYSA-N 0.000 abstract 1
POYHRXUCNTYVBV-UHFFFAOYSA-N 1,1,5,5-tetrachloropenta-1,4-dien-3-one Chemical compound ClC(Cl)=CC(=O)C=C(Cl)Cl POYHRXUCNTYVBV-UHFFFAOYSA-N 0.000 abstract 1
239000002253 acid Substances 0.000 abstract 1
229940088710 antibiotic agent Drugs 0.000 abstract 1
HQMAOCBLMURRKV-UHFFFAOYSA-N benzene;1,1,1,5,5,5-hexachloropentan-3-one Chemical compound C1=CC=CC=C1.ClC(Cl)(Cl)CC(=O)CC(Cl)(Cl)Cl HQMAOCBLMURRKV-UHFFFAOYSA-N 0.000 abstract 1
FUUIZHICRIXRST-UHFFFAOYSA-N benzene;1,1,5,5-tetrachloropenta-1,4-dien-3-one Chemical compound C1=CC=CC=C1.ClC(Cl)=CC(=O)C=C(Cl)Cl FUUIZHICRIXRST-UHFFFAOYSA-N 0.000 abstract 1
125000005843 halogen group Chemical group 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
238000006243 chemical reaction Methods 0.000 description 13
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
238000004821 distillation Methods 0.000 description 7
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
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 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
238000003756 stirring Methods 0.000 description 6
-1 aroyl halide Chemical class 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
RPZXUSJCSDQNTE-UHFFFAOYSA-N 2,4-dichloro-5-fluorobenzoyl chloride Chemical compound FC1=CC(C(Cl)=O)=C(Cl)C=C1Cl RPZXUSJCSDQNTE-UHFFFAOYSA-N 0.000 description 4
BRLYIXHFSWEYHP-UHFFFAOYSA-N 3,3-dichloro-1-(2,4-dichloro-5-fluorophenyl)prop-2-en-1-one Chemical compound FC1=CC(C(=O)C=C(Cl)Cl)=C(Cl)C=C1Cl BRLYIXHFSWEYHP-UHFFFAOYSA-N 0.000 description 4
MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 4
238000007033 dehydrochlorination reaction Methods 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
239000012043 crude product Substances 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000000725 suspension Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
STBGCAUUOPNJBH-UHFFFAOYSA-N 2,4,5-trifluorobenzoyl chloride Chemical compound FC1=CC(F)=C(C(Cl)=O)C=C1F STBGCAUUOPNJBH-UHFFFAOYSA-N 0.000 description 2
BFZKUJOQSYFVSJ-UHFFFAOYSA-N 3,3-dichloro-1-(2,4,5-trifluorophenyl)prop-2-en-1-one Chemical compound FC1=CC(F)=C(C(=O)C=C(Cl)Cl)C=C1F BFZKUJOQSYFVSJ-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
150000005524 benzylchlorides Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
229960003405 ciprofloxacin Drugs 0.000 description 2
239000013078 crystal Substances 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
235000019441 ethanol Nutrition 0.000 description 2
239000007789 gas Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical group ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 1
IROWIXYGGPOJFJ-UHFFFAOYSA-N 2,3,4,5-tetrachlorobenzoyl chloride Chemical compound ClC(=O)C1=CC(Cl)=C(Cl)C(Cl)=C1Cl IROWIXYGGPOJFJ-UHFFFAOYSA-N 0.000 description 1
XWCKIXLTBNGIHV-UHFFFAOYSA-N 2,3,4,5-tetrafluorobenzoyl chloride Chemical compound FC1=CC(C(Cl)=O)=C(F)C(F)=C1F XWCKIXLTBNGIHV-UHFFFAOYSA-N 0.000 description 1
BONFTDXNVIOQBZ-UHFFFAOYSA-N 2,4,5-trichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC(Cl)=C(Cl)C=C1Cl BONFTDXNVIOQBZ-UHFFFAOYSA-N 0.000 description 1
QRFMMROPLHREJD-UHFFFAOYSA-N 3-(2,4-dichloro-5-fluorophenyl)-3-oxopropanoic acid Chemical compound OC(=O)CC(=O)C1=CC(F)=C(Cl)C=C1Cl QRFMMROPLHREJD-UHFFFAOYSA-N 0.000 description 1
IEDMMCZBIKXEJP-UHFFFAOYSA-N 3-chloro-2,4,5-trifluorobenzoyl chloride Chemical compound FC1=CC(C(Cl)=O)=C(F)C(Cl)=C1F IEDMMCZBIKXEJP-UHFFFAOYSA-N 0.000 description 1
QFOVQRZDLIWFLD-UHFFFAOYSA-N 3-oxo-3-(2,4,5-trifluorophenyl)propanoic acid Chemical compound OC(=O)CC(=O)C1=CC(F)=C(F)C=C1F QFOVQRZDLIWFLD-UHFFFAOYSA-N 0.000 description 1
IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical compound [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
229940124350 antibacterial drug Drugs 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
235000019439 ethyl acetate Nutrition 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
XDKQUSKHRIUJEO-UHFFFAOYSA-N magnesium;ethanolate Chemical compound [Mg+2].CC[O-].CC[O-] XDKQUSKHRIUJEO-UHFFFAOYSA-N 0.000 description 1
KFCKLKBPBMFRCU-UHFFFAOYSA-N methyl 3-(2,4-dichloro-5-fluorophenyl)-3-oxopropanoate Chemical compound COC(=O)CC(=O)C1=CC(F)=C(Cl)C=C1Cl KFCKLKBPBMFRCU-UHFFFAOYSA-N 0.000 description 1
210000002741 palatine tonsil Anatomy 0.000 description 1
UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DD85278635A 1984-07-18 1985-07-16 Verfahren zur herstellung halogenierten aroylessigestern DD237503A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3426482A DE3426482A1 (de)	1984-07-18	1984-07-18	Verfahren zur herstellung von halogenierten aroylessigestern

Publications (1)

Publication Number	Publication Date
DD237503A5 true DD237503A5 (de)	1986-07-16

Family

ID=6240967

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD85278635A DD237503A5 (de)	1984-07-18	1985-07-16	Verfahren zur herstellung halogenierten aroylessigestern

Country Status (12)

Country	Link
US (1)	US4611080A (da)
EP (1)	EP0168732B1 (da)
JP (1)	JPS6136246A (da)
KR (1)	KR910008372B1 (da)
AT (1)	ATE35980T1 (da)
DD (1)	DD237503A5 (da)
DE (2)	DE3426482A1 (da)
DK (1)	DK325885A (da)
ES (1)	ES8604482A1 (da)
HU (1)	HU193335B (da)
IL (1)	IL75810A (da)
ZA (1)	ZA855388B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4788320A (en) *	1986-01-20	1988-11-29	Kyorin Pharmaceutical Co., Ltd.	Benzoylacetic acid ester derivatives and process for their preparations
EP0449445A3 (en) *	1990-03-27	1993-08-25	Pfizer Inc.	Preparation of beta-ketoesters useful in preparing quinolone antibiotics

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2848459A (en) *	1957-04-25	1958-08-19	Olin Mathieson	Carbamic acid esters
US3818072A (en) *	1971-12-01	1974-06-18	Richardson Merrell Inc	Alkyl substituted-benzoylacetates antilipemic agents
DE2536977A1 (de) *	1975-08-20	1977-03-03	Bayer Ag	Vinyl(di- bzw. tri)thiophosphor (phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
DE2537047A1 (de) *	1975-08-20	1977-03-03	Bayer Ag	Vinylthionophosphorsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide
DE3142854A1 (de) *	1981-10-29	1983-05-11	Bayer Ag, 5090 Leverkusen	1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-piperazino-chinolin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel
DE3142856A1 (de) *	1981-10-29	1983-05-11	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von 2,4-dichlor-5-fluor-benzoylchlorid
DE3248505A1 (de) *	1982-12-29	1984-07-05	Bayer Ag, 5090 Leverkusen	1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7(4- (oxoalkyl)-1-piperazinyl/-3-chinolincarbonsaeuren und ihre derivate, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel

1984
- 1984-07-18 DE DE3426482A patent/DE3426482A1/de not_active Withdrawn
1985
- 1985-07-06 DE DE8585108397T patent/DE3563962D1/de not_active Expired
- 1985-07-06 EP EP85108397A patent/EP0168732B1/de not_active Expired
- 1985-07-06 AT AT85108397T patent/ATE35980T1/de not_active IP Right Cessation
- 1985-07-11 ES ES545080A patent/ES8604482A1/es not_active Expired
- 1985-07-12 US US06/754,692 patent/US4611080A/en not_active Expired - Fee Related
- 1985-07-15 IL IL75810A patent/IL75810A/xx unknown
- 1985-07-16 KR KR1019850005068A patent/KR910008372B1/ko not_active Expired
- 1985-07-16 DD DD85278635A patent/DD237503A5/de not_active IP Right Cessation
- 1985-07-17 ZA ZA855388A patent/ZA855388B/xx unknown
- 1985-07-17 HU HU852749A patent/HU193335B/hu unknown
- 1985-07-17 JP JP15616885A patent/JPS6136246A/ja active Pending
- 1985-07-17 DK DK325885A patent/DK325885A/da unknown

Also Published As

Publication number	Publication date
EP0168732A2 (de)	1986-01-22
ES8604482A1 (es)	1986-02-01
DE3426482A1 (de)	1986-01-30
IL75810A (en)	1988-12-30
HU193335B (en)	1987-09-28
IL75810A0 (en)	1985-11-29
ZA855388B (en)	1986-02-26
EP0168732B1 (de)	1988-07-27
EP0168732A3 (en)	1987-03-25
HUT38603A (en)	1986-06-30
KR910008372B1 (ko)	1991-10-12
ATE35980T1 (de)	1988-08-15
US4611080A (en)	1986-09-09
ES545080A0 (es)	1986-02-01
DE3563962D1 (en)	1988-09-01
JPS6136246A (ja)	1986-02-20
DK325885D0 (da)	1985-07-17
DK325885A (da)	1986-01-19
KR860001046A (ko)	1986-02-22

Legal Events

Date	Code	Title	Description
2001-10-25	ENJ	Ceased due to non-payment of renewal fee

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