DK150140B - PROCEDURE FOR THE PREPARATION OF OXAZOLIDIN-2,4-DIONE - Google Patents
PROCEDURE FOR THE PREPARATION OF OXAZOLIDIN-2,4-DIONE Download PDFInfo
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- DK150140B DK150140B DK27382A DK27382A DK150140B DK 150140 B DK150140 B DK 150140B DK 27382 A DK27382 A DK 27382A DK 27382 A DK27382 A DK 27382A DK 150140 B DK150140 B DK 150140B
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- Prior art keywords
- methyl
- dione
- dichlorophenyl
- halogen
- phenyl
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
- C07D263/44—Two oxygen atoms
Abstract
Description
i 150U0in 150U0
Opfindelsen angår en særlig fremgangsmåde af den i krav' l's indledning angivne art til fremstilling af oxazolidin- 2,4-dioner ved omsætning af substituerede amider med aromatiske kulsyreestestere.The invention relates to a particular process of the kind set forth in the preamble of claim 1 for the preparation of oxazolidine-2,4-dione by reacting substituted amides with aromatic carbonic acid testers.
5 Det er velkendt, at oxazolidin-2,4-dioner fremstilles ved omsætning af isocyanater med 2-hydroxycarboxylsyreestere (DE-AS 18 11 843, DE-OS 20 22 494, DE-OS 22 07 576)-It is well known that oxazolidine-2,4-dione is prepared by reacting isocyanates with 2-hydroxycarboxylic acid esters (DE-AS 18 11 843, DE-OS 20 22 494, DE-OS 22 07 576) -
Det er yderligere kendt at omsætte et substitueret urin-stofderivåt med diphenylcarbonat til en 6-leddet ring, 10 der indeholder 3 nitrogenatomer i ringen (fransk patent-skrift nr. 2 316 239). Herudover er det kendt at omsætte et primært hydroxycarboxylsyreamid med dialkylcarbonat og en støkiometrisk mængde af et metalalkoholat i to trin til en oxazolidindion (USA patentskrifterne nr. 2 338 220 og 15 nr. 2 909 467).It is further known to react a substituted urea substance diphenyl carbonate to a 6-membered ring containing 10 nitrogen atoms in the ring (French Patent No. 2,316,239). In addition, it is known to react a primary hydroxycarboxylic acid amide with dialkyl carbonate and a stoichiometric amount of a two-step metal alcoholate to an oxazolidinedione (U.S. Patent Nos. 2,338,220 and 15,909,467).
Det har nu vist sig, at man i særdeles godt udbytte kan fremstille en oxazolidin-2,4-dion med formlen 0 r -n>V:It has now been found that in very good yield an oxazolidine-2,4-dione of the formula 0r -n> V can be prepared:
0 \ R0 \ R
hvori R·*· betegner en naphthylgruppe eller en eventuelt med en eller flere halogenatomer eller med methyl eller methoxy 2 20 substitueret phenylgruppe, R betegner hydrogen eller en alkyl- gruppe med 1-4 C-atomer, halogen eller en vinylgruppe eller methoxymethyl eller carboethoxy, og har de samme betyd-2 2 3 ninger som R , idet R og R er ens eller forskellige, 2 3 eller R og R er forbundet med hinanden og betegner en 2 150140 methylengruppe, dersom man omsætter et hydroxycarboxylsy-reamid med et diorganylcarbonat ved en fremgangsmåde, der er ejendommelig ved, at man omsætter et amid med formlen:represents a naphthyl group or an optionally having one or more halogen atoms or with methyl or methoxy substituted phenyl group, R represents hydrogen or an alkyl group having 1-4 C atoms, halogen or a vinyl group or methoxymethyl or carboethoxy and have the same meanings as R, wherein R and R are the same or different, 2 3 or R and R are linked to each other and denote a methylene group if reacting a hydroxycarboxylic acid amide with a diorganyl carbonate by a process peculiar to reacting an amide of the formula:
R1-NH-C0-CCR1-NH-C 0-CC
1 \ 31 \ 3
OHOH
12 3 hvori R , R og R har ovennævnte betydninger, ved en tem-5 peratur mellem 50 og 250°C, med en aromatisk kulsyreester med formlen R4-0~C-0-R5 il 0 Λ hvori R betegner en eventuelt med methyl eller halogen substitueret phenylgruppe, og R^ har samme betydning som 4 4 5 R , eller R og R betegner sammen 1,2-phenylengruppen, 10 og at man fraskiller de ved omsætningen opståede phenoler 4 5 R OH og R OH, fortrinsvis ved afdestillation.Wherein R, R and R have the above meanings, at a temperature between 50 and 250 ° C, with an aromatic carbonic acid ester of the formula R4-O-C-O-R5 in 0 Λ wherein R represents an optionally with methyl or halogen substituted phenyl group and R 1 has the same meaning as 4 4 5 R, or R and R together represent the 1,2-phenylene group, 10 and the phenols resulting from the reaction are separated from R 5 OH and R OH, preferably by distillation. .
De forskellige substituenter har f.eks. følgende betydninger: R^ er f.eks. phenyl, naphthyl, 2-, 3- og 4-fluor-phenyl, 2-, 3- og 4-chlorphenyl, 2-, 3- og 4-bromphenyl, 15 2,3-dichlorphenyl, 2,3,6-trichlorphenyl, 2-, 3- og 4- methoxyphenyl, 2-, 3- og 4-methylphenyl, 3,4-dihclorphen-yl, 2,6-dichlorphenyl, 2,3,4-trichlorphenyl, 2,3,5-trichlor-phenyl og foretrukkent 3,5-dichlorphenyl.The various substituents e.g. the following meanings: R phenyl, naphthyl, 2-, 3- and 4-fluoro-phenyl, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-bromophenyl, 2,3-dichlorophenyl, 2,3,6-trichlorophenyl , 2-, 3- and 4-methoxyphenyl, 2-, 3- and 4-methylphenyl, 3,4-dichlorophenyl, 2,6-dichlorophenyl, 2,3,4-trichlorophenyl, 2,3,5-trichloro -phenyl and preferably 3,5-dichlorophenyl.
2 3 R og R er f.eks. hydrogen eller vinyl eller alkyl f.eks.2 3 R and R are e.g. hydrogen or vinyl or alkyl e.g.
3 150140 methyl, ethyl eller methoxymethyl eller carboethoxy.Methyl, ethyl or methoxymethyl or carboethoxy.
R4 og R5 betegner f.eks. 4-methylphenyl, 4-chlorphenyl 4 5 eller fortrinsvis phenyl, ellerR og R betegner sammen 1,2-phenylen ).R4 and R5 represent e.g. 4-methylphenyl, 4-chlorophenyl or preferably phenyl, or R and R together represent 1,2-phenylene).
5 For at gennemføre omsætningen er en forhøjet temperatur mellem 50 og 250°C, fortrinsvis 120 og 170°C nødvendig.In order to effect the reaction, an elevated temperature between 50 and 250 ° C, preferably 120 and 170 ° C is required.
For omsætningen er det vigtigt, at den aromatiske kulsyre-ester er særdeles ren (f.eks. fri for chlormyresyrepheny1-ester og sure forureninger).For the reaction, it is important that the aromatic carbonic acid ester is extremely pure (eg free of chloroformic acid phenyl ester and acidic contaminants).
10 Reaktionen kan gennemføres uden katalysator. For at få om muligt kvantitative og hurtigere omsætninger, dvs. opnå høje rumfang-tids-udbytter, kan det være en fordel at tilsætte følgende basiske katalysatorer: alkalimetalalkoho-later som natriummethylat, natriumethylat, aminer f.eks.The reaction can be carried out without a catalyst. To get quantitative and faster turnover, if possible. obtaining high volume yields, it may be advantageous to add the following basic catalysts: alkali metal alcohols such as sodium methylate, sodium ethylate, amines e.g.
15 tertiære aminer (tripropylamin, tributylamin), alkalime-talphenolater med formlen R40pMe+ λ hvori R har ovennævnte betydning, og Me betegner et alkalimetal (f.eks. natriumphenolat). Tilsætningen af katalysator sker f.eks. i en mængde på fra 0,01 molprocent til 20 0,1 molprocent beregnet på amidet.15 tertiary amines (tripropylamine, tributylamine), alkali metal phenolates of the formula R40pMe + λ in which R is as defined above and Me represents an alkali metal (e.g., sodium phenolate). The addition of catalyst takes place e.g. in an amount of from 0.01 mole percent to 0.1 mole percent based on the amide.
Omsætningen gennemføres med fordel uden opløsningsmiddel.The reaction is advantageously carried out without solvent.
Dersom der anvendes opløsningsmiddel, skal dettes kogepunkt 4 5 ligge over phenolernes R OH og R OH.If solvent is used, its boiling point 45 should be above the R OH and R OH of the phenols.
4 1501604 150160
Det er overraskende, at omsætningen med diarylcarbonat sker meget hurtigt og uden katalysator.Unsurprisingly, the reaction with diaryl carbonate occurs very quickly and without catalyst.
Vigtigt for et godt udbytte ved omsætningen er det, at man fraskiller de ved omsætningen opståede phenoler R^OH og 5 R^OH om muligt kvantitativt, fortrinsvis ved afdestilla-tion, og at man sørger for, at det som udgangsprodukt anvendte diarylcarbonat ikke destillerer med. Til dette formål er det fordelagtigt at anvende destillationskolonner med fyldlegemer.Important for a good yield in the reaction is that, if possible, the phenols R with. For this purpose, it is advantageous to use distillation columns with fillers.
10 De afdestillerede phenoler R40H og R50H fås så rene, at de atter kan anvendes som udgangsstoffer ved frem-4 5 , stillingen af R -0-C-0-R (recirkulation).10 The distilled phenols R40H and R50H are obtained so that they can again be used as starting substances at the forward-4.5, position of R-0-C-0-R (recirculation).
ti 0ti 0
Omsætningen kan gennemføres ved normalt tryk} et vacuum på ca. 1 mbar til 950 mbar kan være en fordel for at sænke 15 destillationstemperaturen.The reaction can be carried out at normal pressure} 1 mbar to 950 mbar can be an advantage in lowering the distillation temperature.
De som udgangsprodukter anvendte amider fås f.eks. som biprodukter ved den velkendte fremstilling af de tilsvarende oxazolidin-2,4-dioner.The amides used as starting products are obtained e.g. as by-products of the well-known preparation of the corresponding oxazolidine-2,4-dione.
Amiderne fås også ved alkoholyse af de tilsvarende oxazoli-20 din-2,4-dioner med ethylenglycol eller glycerol.The amides are also obtained by alcoholysis of the corresponding oxazolidine-2,4-dione with ethylene glycol or glycerol.
Fremgangsmåden ifølge opfindelsen kan alment afbildes således: 150140 5 ^ R2 R^NH-CO-C , + R^-O-C-O-R5 I fl OH K 0 0 1 f-0 2 4 5The process according to the invention can generally be depicted as follows: 1 R 2 R 2 NH-CO-C, + R 2 -O-C-O-R 5 In fl OH K 0 0 1 f-0 2 4 5
R + R 0H + R 0HR + R OH + R OH
OR3 0 4 " 5OR3 0 4 "5
Den billigere reaktionsdeltager f.eks. R -O-C-O-R kan anvendes i overskud (f.eks. 1,1 mol ester til 1 mol amid).The cheaper reaction participant e.g. R -O-C-O-R can be used in excess (e.g., 1.1 mole of ester to 1 mole of amide).
Følgende eksempler belyser gennemførelsen af den omhandle-5 de fremgangsmåde nærmere: EKSEMPEL 1 Cl (5>-U^ + W-!r006H5 / 0 OH 0The following examples illustrate the implementation of the present process in greater detail: EXAMPLE 1 Cl (5> -U ^ + W-! R006H5 / 0 OH 0
ClCl
Cl 0 ''Cl 0 ''
^0)-+ 2 wH^ 0) - + 2 wH
Cl O CH3 26 g (0,1 mol) N-(3,5-dichlorphenyl)-2-hydroxy-2-methyl-3-butensyreamid og 21,4 g (0,1 mol) diphenylcarbonåt opvarmes til 160-165 °C. Ved et tryk på ca. 30 mbar destillerer 10 18,4 g phenol over (overgangstemperatur 88-95 °C). Den til bageblevne smelte afkøles til 80 °C, og der tilsættes 25 ml methanol. Der omrøres 2 timer og afkøles til 5 °C. Efter 150140 6 afsugning vaskes der to gange med 10 ml methanol per gang, og herefter vaskes med 50 ml vand.ClO CH3 26 g (0.1 mole) of N- (3,5-dichlorophenyl) -2-hydroxy-2-methyl-3-butenoic acid amide and 21.4 g (0.1 mole) of diphenylcarbonate are heated to 160-165 ° C. At a pressure of approx. 30 mbar distills over 18.4 g of phenol (transition temperature 88-95 ° C). The residual melt is cooled to 80 ° C and 25 ml of methanol is added. Stir for 2 hours and cool to 5 ° C. After extraction, wash twice with 10 ml of methanol at a time and then wash with 50 ml of water.
Udbytte: 26,7 g 3-(3,5-dichlorphenyl)-5-methyl-5-vinyl-l,3-oxazolidin-2,4-dion, indhold 99% = 92,4¾ udbytte beregnet 5 for et 100¾ produkt. Smeltepunkt 111 °C, rent ved tyndt- lagschromatografi.Yield: 26.7 g of 3- (3,5-dichlorophenyl) -5-methyl-5-vinyl-1,3-oxazolidine-2,4-dione, content 99% = 92.4¾ yield calculated 5 for a 100¾ product . Melting point 111 ° C, pure by thin layer chromatography.
EKSEMPEL 2 3-(3,5-dichlorphenyl)-5-methy1-5-methoxymethyl-oxazoli-' din-2,4-dionEXAMPLE 2 3- (3,5-Dichlorophenyl) -5-methyl-5-methoxymethyl-oxazolidine-2,4-dione
Cl H ^ {oVf-i,--f CH3 + C6H5°-C-2C6H5 C1>^ o OH 0 oCl H ^ {oVf-i, - f CH3 + C6H5 ° -C-2C6H5 C1> ^ o OH 0 o
Vr\ Ao 1Fr \ Ao 1
___j CH3 + 2 CgH^OH___j CH3 + 2 CgH ^ OH
Cl 0 0NCl 0 0 N
CH3 10 27,8 g (0,1 mol) N-(3,5-dichlorphenyl)-2-hydroxy-2-meth- oxymethyl-propansyreamid, 21,4 g (0,1 mol) diphenylcarbo-nat og 0,7 g (0,01 mol) natriumethylat opvarmes ved 140-145 °C. Ued 22 mbar afdestilleres i en time den opståede phenol (overgang 88-102 °C). Remanensen afkøles til 70 QC, 15 og der tilsættes 75 ml methanol og omrøres to timer ved 15 °C. Efter frasugning vaskes to gange med 10 ml vand per gang og tørres.CH3 10 27.8 g (0.1 mole) of N- (3,5-dichlorophenyl) -2-hydroxy-2-methoxymethylpropanoic acid amide, 21.4 g (0.1 mole) of diphenyl carbonate and 0, 7 g (0.01 mole) of sodium ethylate are heated at 140-145 ° C. Below 22 mbar, the resulting phenol is distilled off for one hour (transition 88-102 ° C). The residue is cooled to 70 ° C, 15 ml and 75 ml of methanol are added and stirred for two hours at 15 ° C. After suctioning, wash twice with 10 ml of water at a time and dry.
Udbytte: 13 g 3-(3,5-dichlorphenyl)-5-methyl-5-methoxy-methyloxazolidin-2,4-dion, hvilket svarer til 85,5¾ ud-20 bytte. Smeltepunkt 112 °C (ren ved tyndtlagschromatografi).Yield: 13 g of 3- (3,5-dichlorophenyl) -5-methyl-5-methoxy-methyloxazolidine-2,4-dione, which corresponds to 85.5¾ yield. Melting point 112 ° C (pure by thin layer chromatography).
7 1501407 150140
Indhold: 100% (bestemt ved højtryksvæskechromatografi).Content: 100% (determined by high-pressure liquid chromatography).
Følgende metoder belyser fremstillingen af amiderne ved alkoholyse.The following methods illustrate the preparation of the amides by alcoholysis.
METODE 1 5 N-(3,5-dichlorphenyl)-2-hydroxy-2-methyl-3-butensyreamid 01 0 _METHOD 1 N- (3,5-dichlorophenyl) -2-hydroxy-2-methyl-3-butenoic acid amide
V—\ ,Ϊ-O + HO ^OHV— \, Ϊ-O + HO ^ OH
Cl^ 0 CE3Cl3 CE3
Cl C Hg (oWK*Cl C Hg (oWK *
s—' 0 OHs— '0 OH
Cl 214,5 g (0,75 mol) 3-(3,5-dichlorphenyl)-5-methyl-5-vinyl- 1,3-oxazolidin-2,4-dion omrøres i to timer med 750 ml (13,5 mol) ethylenglycol og 8,25 g (0,056 mol) tripropylamin ved 150 °C.C 214.5 g (0.75 mol) of 3- (3,5-dichlorophenyl) -5-methyl-5-vinyl-1,3-oxazolidine-2,4-dione is stirred for two hours with 750 ml (13, 5 mol) ethylene glycol and 8.25 g (0.056 mol) of tripropylamine at 150 ° C.
10 Ved ca. 80 °C afdestilleres herefter ved rotationsfordamp ning med vacuumpumpe (ca. 0,2 mbar) den tilbageblevne ethylenglycol. Remanensen, der udkrystalliserer ved henstand natten over, vejer 198 g, og omkrystalliseres med 150 ml toluen. Der fås 128 g N-(3,5-dichlorphenyl)-2-hydroxy-15 2-methyl-3-butensyreamid. Smeltepunkt 116 °C, IR- og H-NMR-spektrene er i overensstemmelse med strukturen.10 At approx. 80 ° C is then distilled off by vacuum evaporation with a vacuum pump (about 0.2 mbar) of the remaining ethylene glycol. The residue, which crystallizes on standing overnight, weighs 198 g and is recrystallized with 150 ml of toluene. 128 g of N- (3,5-dichlorophenyl) -2-hydroxy-2-methyl-3-butenoic amide are obtained. Melting point 116 ° C, IR and H NMR spectra are consistent with structure.
Analyse : C H 0 N Cl fundet : 50,9 4,4 12,3 5,9 27,2 beregnet: 50,8 4,2 12,3 5,4 27,3Analysis: C H 0 N Cl found: 50.9 4.4 12.3 5.9 27.2 Calculated: 50.8 4.2 12.3 5.4 27.3
Claims (3)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3102359A DE3102359A1 (en) | 1981-01-24 | 1981-01-24 | METHOD FOR PRODUCING OXAZOLIDINE-2,4-DIONES |
| DE3102359 | 1981-01-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK27382A DK27382A (en) | 1982-07-25 |
| DK150140B true DK150140B (en) | 1986-12-15 |
| DK150140C DK150140C (en) | 1987-06-15 |
Family
ID=6123295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK027382A DK150140C (en) | 1981-01-24 | 1982-01-22 | PROCEDURE FOR THE PREPARATION OF OXAZOLIDIN-2,4-DIONE |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0056966B1 (en) |
| AT (1) | ATE9801T1 (en) |
| DE (2) | DE3102359A1 (en) |
| DK (1) | DK150140C (en) |
| GR (1) | GR77325B (en) |
| IE (1) | IE52262B1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19613333A1 (en) * | 1996-04-03 | 1997-10-09 | Bayer Ag | Process for the preparation of oxazolidine-2,4-diones |
| JP2015504040A (en) * | 2011-12-15 | 2015-02-05 | コルゲート・パーモリブ・カンパニーＣｏｌｇａｔｅ−Ｐａｌｍｏｌｉｖｅ Ｃｏｍｐａｎｙ | Aqueous oral care composition |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2338220A (en) * | 1942-01-31 | 1944-01-04 | Mallinckrodt Chemical Works | Process of making oxazolidinediones |
| US2909467A (en) * | 1958-07-09 | 1959-10-20 | Us Vitamin Pharm Corp | 3-(d-alpha-methylphenethyl)-5-methyl-1, 3-oxazolidine-2, 4-dione |
| US2928840A (en) * | 1958-11-26 | 1960-03-15 | Us Vitamin Pharm Corp | 3-(o-substituted phenyl) oxazolidinediones and process therefor |
| DE1813434A1 (en) * | 1968-12-07 | 1970-06-25 | Bayer Ag | Process for the preparation of omicron-hydroxy-aralkyl ethers |
| DE2527677A1 (en) * | 1975-06-21 | 1977-01-20 | Bayer Ag | PROCESS FOR THE PREPARATION OF 2,4-DIOXO-1,2,3,4-TETRAHYDRO-S-TRIAZINO- SQUARE BRACKET TO 1,2-A SQUARE BRACKET TO -BENZIMIDAZOLE |
| DE2813873A1 (en) * | 1978-03-31 | 1979-10-11 | Basf Ag | PROCESS FOR THE PRODUCTION OF OXAZOLIDINE-2,4-DIONEN |
| DE2827414A1 (en) * | 1978-06-22 | 1980-01-10 | Basf Ag | METHOD FOR PRODUCING OXAZOLIDINE-2,4-DIONES |
-
1981
- 1981-01-24 DE DE3102359A patent/DE3102359A1/en not_active Withdrawn
- 1981-12-17 GR GR66823A patent/GR77325B/el unknown
-
1982
- 1982-01-18 DE DE8282100306T patent/DE3260914D1/en not_active Expired
- 1982-01-18 AT AT82100306T patent/ATE9801T1/en not_active IP Right Cessation
- 1982-01-18 EP EP82100306A patent/EP0056966B1/en not_active Expired
- 1982-01-22 IE IE138/82A patent/IE52262B1/en unknown
- 1982-01-22 DK DK027382A patent/DK150140C/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3260914D1 (en) | 1984-11-15 |
| IE52262B1 (en) | 1987-08-19 |
| EP0056966A1 (en) | 1982-08-04 |
| IE820138L (en) | 1982-07-24 |
| DE3102359A1 (en) | 1982-08-19 |
| ATE9801T1 (en) | 1984-10-15 |
| GR77325B (en) | 1984-09-11 |
| DK27382A (en) | 1982-07-25 |
| EP0056966B1 (en) | 1984-10-10 |
| DK150140C (en) | 1987-06-15 |
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