DE3228101A1 - Process for the preparation of sulphonyl isocyanates - Google Patents
Process for the preparation of sulphonyl isocyanatesInfo
- Publication number
- DE3228101A1 DE3228101A1 DE19823228101 DE3228101A DE3228101A1 DE 3228101 A1 DE3228101 A1 DE 3228101A1 DE 19823228101 DE19823228101 DE 19823228101 DE 3228101 A DE3228101 A DE 3228101A DE 3228101 A1 DE3228101 A1 DE 3228101A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- tertiary amine
- preparation
- optionally
- lower alkyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 10
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 8
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000003456 sulfonamides Chemical class 0.000 claims abstract description 4
- 230000003197 catalytic effect Effects 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical class [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical group C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- -1 aliphatic amines Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- OUPLTJDZPQZRBW-UHFFFAOYSA-N n-(oxomethylidene)methanesulfonamide Chemical compound CS(=O)(=O)N=C=O OUPLTJDZPQZRBW-UHFFFAOYSA-N 0.000 description 1
- BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Die Erfindung betrifft ein Verfahren, das es er-The invention relates to a method that it
möglicht, Sulfonylisocyanate in guter Ausbeute herzustellen.enables sulfonyl isocyanates to be produced in good yield.
Es ist bekannt, daß Organosulfonylisocyanate durch Phosgenierung bei erhöhter Temperatur (DE-PS 817 602), durch Umsetzung von Organosulfonylchloriden mit Cyanaten (Ber. Deut.Chem. Ges. 36, 3214 (1903)) oder durch Phosgenierung von N-Alkyl-N'-Arylsulfonylharnstoffen bei erhöhter Temperatur gewonnen werden können. Die Ausbeuten dieser Verfahren sind jedoch unbefriedigend. Dasselbe gilt von dem JUngsten Verfahren, das in der Umsetzung von Sulfonamiden mit Chlorsulfonylisocyanat besteht (Chem. Ber. 107, 706 ff.It is known that organosulfonyl isocyanates by phosgenation elevated temperature (DE-PS 817 602), by reacting organosulfonyl chlorides with cyanates (Ber. Deut.Chem. Ges. 36, 3214 (1903)) or by phosgenation of N-alkyl-N'-arylsulfonylureas can be obtained at elevated temperature. However, the yields of these processes are unsatisfactory. The same is true of that Recent process used in the reaction of sulfonamides with chlorosulfonyl isocyanate exists (Chem. Ber. 107, 706 ff.
(1974)); hier werden Ausbeuten zwischen 18,2 und 37,5 der Theorie angegeben.(1974)); here yields between 18.2 and 37.5 of theory specified.
Wie nun gefunden wurde, können Sulfonylisocyanate der Formel R - SO2 - NCO (I), in der R £r einen gegebenenfalls ein- oder mehrfach niederalkoxysubstituierten geradkettigen oder verzweigten Cl-Clb-Alkylrest oder einen gegebenenfalls ein- oder mehrfach durch Halogen, Nitro, Niederalkyl oder Niederalkoxy, Trifluormethyl oder Niederalkoxycarbonyl substituierten Benzylrest steht, überraschenderweise in guter Ausbeute erhalten werden, wenn man die Umsetzung entsprechender Sulfonsäureamide mit Chlorsulfonylisocyanat in Gegenwart katalytischer Mengen tertiärer Amine durchfuhrt.As has now been found, sulfonyl isocyanates of the formula R - SO2 - NCO (I), in which R £ r is an optionally mono- or polysubstituted lower alkoxy straight-chain or branched Cl-Clb-alkyl radical or an optionally mono- or several times by halogen, nitro, lower alkyl or lower alkoxy, trifluoromethyl or Lower alkoxycarbonyl substituted benzyl radical, surprisingly in good Yield can be obtained if you implement the corresponding sulfonic acid amides with chlorosulfonyl isocyanate in the presence of catalytic amounts of tertiary amines.
Als katalytisch wirkende tertiare Amine fur das erfindungsgemäße Verfahren geeignet sind alle tertiären Amine, die unter den Reaktionsbedingungen ausreichend beständig sind. Zu nennen sind hier aliphatische Amine wie Triethylamin, Tripropylamin, cyclische Amine wie N-Methylpiperidin, l,4-Diazabicyclo (2,2,2)-octan, N,N'-Dimethylpiperazin, gemischt substituierte Amine wie N,N Dimethylanilin, Pyridin, Picoline, 4-N,N-Dimethylaminopyridin, Lutidin.As catalytically active tertiary amines for the process according to the invention all tertiary amines are suitable under the reaction conditions sufficient are persistent. Mention should be made here of aliphatic amines such as triethylamine, tripropylamine, cyclic amines such as N-methylpiperidine, 1,4-diazabicyclo (2,2,2) -octane, N, N'-dimethylpiperazine, mixed substituted amines such as N, N dimethylaniline, pyridine, picolines, 4-N, N-dimethylaminopyridine, Lutidine.
Die Menge des Amins kann in weiten Grenzen variiert werden. Im allgemeinen werden pro Mol Sulfonamid 0,001 bis 0,2, vorzugsweise 0,005 bis 0,1 Mol tertiäres Amin eingesetzt.The amount of amine can be varied within wide limits. In general 0.001 to 0.2, preferably 0.005 to 0.1 mol of tertiary per mole of sulfonamide Amine used.
Die als Ausgangsstoffe dienenden Sulfonamide entsprechen der Formel R - S°2 - NHR' (ru), worin R die obige Bedeutung hat und R' für Wasserstoff oder einen niederen Alkylrest steht. Die Verbindungen der Formel II und Chlorsulfonylisocyanat werden vorzugsweise im Molverhältnis 1 : 1 eingesetzt, doch sind Abweichungen von diesem Verhältnis gewünschtenfalls möglich, insbesondere ein Uberschuß an Chlorsulfonylisocyanat.The sulfonamides used as starting materials correspond to the formula R - S ° 2 - NHR '(ru), where R has the above meaning and R' is hydrogen or represents a lower alkyl radical. The compounds of formula II and chlorosulfonyl isocyanate are preferably used in a molar ratio of 1: 1, but there are deviations from this ratio is possible if desired, in particular an excess of chlorosulfonyl isocyanate.
Die Reaktion erfolgt bei erhöhter Temperatur in Lösungsmitteln, die unter den Reaktionsbedingungen hinreichend beständig sind, z.B. in aromatischen Kohlenwasserstoffen wie Benzol, Toluol, Xylol, chlorierten Aromaten wie Chlorbenzol und Dichlorbenzolen, Aliphaten wie n-Octan oder Pentachlorethan.The reaction takes place at elevated temperature in solvents that are sufficiently stable under the reaction conditions, e.g. in aromatic Hydrocarbons such as benzene, toluene, xylene, chlorinated aromatics such as chlorobenzene and dichlorobenzenes, aliphatics such as n-octane or pentachloroethane.
Die geeigneten Reaktionstemperaturen liegen im allgemeinen im Bereich zwischen 50 und 1300C. Je nach der gewünschten Reaktionstemperatur werden Lösungsmittel oder Lösungsmittelgemische mit entsprechend hohen Siedetemperaturen verwendet. Zweckmäßig arbeitet man bei der Siedetemperatur des Reaktionsgemischs, die durch die Wahl des Lösungsmittels gesteuert werden kann.The suitable reaction temperatures are generally in the range between 50 and 1300C. Depending on the desired reaction temperature, solvents are used or solvent mixtures with accordingly high boiling temperatures used. It is expedient to work at the boiling point of the reaction mixture, which can be controlled by the choice of solvent.
Unter Niederalkyl" bzw. "Niederalkoxy" im Sinne der Erfindung sind solche Gruppen mit 1 bis 4 C-Atomen zu verstehen. Halogen bedeutet Fluor, Chlor, Brom und Jod.Under lower alkyl "or" lower alkoxy "for the purposes of the invention are to understand such groups with 1 to 4 carbon atoms. Halogen means fluorine, chlorine, Bromine and iodine.
Soweit es sich bei den Substituenten um Halogenatome handelt, sind Fluor, Chlor und Brom bevorzugt, im Fall der Alkyl- und Alkoxygruppen solche mit 1 - 2 C-Atomen.As far as the substituents are halogen atoms, are Fluorine, chlorine and bromine are preferred, in the case of the alkyl and alkoxy groups those with 1 - 2 carbon atoms.
Die erfindungsgemäß erhältlichen Organosulfonylisocyanate sind wertvolle Zwischenprodukte, beispielsweise für die Herstllung von Arzneistoffen und Pestiziden.The organosulfonyl isocyanates obtainable according to the invention are valuable Intermediate products, for example for the manufacture of pharmaceuticals and pesticides.
Die nachstehenden Beispiele sollen das erfindungs gemäße Verfahren erld'utern, ohne es zu begrenzen; entsprechend den obigen Ausführun-gen sind insbesondere hinsichtlich der Reaktionstemperatur und der Lösungsmittel, aber auch der Katalysatoren Abwandlungen möglich.The following examples are intended to the fiction, contemporary method erld'utern without limiting it; in accordance with the above statements are in particular with regard to the reaction temperature and the solvents, but also the catalysts Modifications possible.
Beispiel Methylsulfonylisocyanat 9,5 g (0,1 mol) Methansulfonsäureamid und 0,5 g 1,4"Diazabicyclo(2,2,2)-octan in 100 ml Chiorbenzol werden vorgelegt. Unter Rühren werden 10 ml (0,11 mol) Chlorsulfonylisocyanat zugegeben. Die Mischung wird bei 95 - 100°C 1 1/2 Stunden gerührt und dann abgekühlt. Man dekantiert vom ungelösten ab und engt die Lösung am Rotationaverdampfer ein. Der Rückstand wird fraktioniert destilliert oder auch roh zur weiteren Umsetzung verwendet.Example methyl sulfonyl isocyanate 9.5 g (0.1 mol) methanesulfonic acid amide and 0.5 g of 1,4 "diazabicyclo (2,2,2) octane in 100 ml of chlorobenzene are presented. 10 ml (0.11 mol) of chlorosulfonyl isocyanate are added with stirring. The mixture is stirred at 95-100 ° C for 1 1/2 hours and then cooled. One decants from undissolved and the solution is concentrated on a rotary evaporator. The residue will fractionally distilled or used raw for further implementation.
Ausbeute 47 % d.Th., Kp. 60 - 100°C/0,3 - 0,6 mbar.Yield 47% of theory, b.p. 60-100 ° C / 0.3-0.6 mbar.
Zu einem ganz ähnlichen Ergebnis kommt man, wenn als Katalysator Triethylamin oder N,N'-Dimethylpiperazin eingesetzt wird.A very similar result is obtained when triethylamine is used as the catalyst or N, N'-dimethylpiperazine is used.
Entsprechend dem vorstehenden Beispiel lassen sich die Verbindungen
der nachstehenden Tabelle 1 erhalten:
Tabelle 1 Verbindungen der
Formel R - SO2 - NCO
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823228101 DE3228101A1 (en) | 1982-07-28 | 1982-07-28 | Process for the preparation of sulphonyl isocyanates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823228101 DE3228101A1 (en) | 1982-07-28 | 1982-07-28 | Process for the preparation of sulphonyl isocyanates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3228101A1 true DE3228101A1 (en) | 1984-02-02 |
Family
ID=6169478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823228101 Withdrawn DE3228101A1 (en) | 1982-07-28 | 1982-07-28 | Process for the preparation of sulphonyl isocyanates |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3228101A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0271780A3 (en) * | 1986-12-16 | 1989-08-09 | Bayer Ag | Substituted 1-benzylsulfonyl-3-heteroaryl(thio) urea |
| US5294741A (en) * | 1991-02-25 | 1994-03-15 | Hoechst Aktiengesellschaft | Continuous process for the preparation of sulfonylisocyanates |
-
1982
- 1982-07-28 DE DE19823228101 patent/DE3228101A1/en not_active Withdrawn
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0271780A3 (en) * | 1986-12-16 | 1989-08-09 | Bayer Ag | Substituted 1-benzylsulfonyl-3-heteroaryl(thio) urea |
| US4927454A (en) * | 1986-12-16 | 1990-05-22 | Bayer Aktiengesellschaft | Substituted 1-benzylsulphonyl-3-heteroaryl-(thio)urea herbicides |
| US4990637A (en) * | 1986-12-16 | 1991-02-05 | Bayer Aktiengesellschaft | 1-benzylsulphonyl-3-heteroaryl-(thio)urea herbicides |
| US5294741A (en) * | 1991-02-25 | 1994-03-15 | Hoechst Aktiengesellschaft | Continuous process for the preparation of sulfonylisocyanates |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |