DD246298A5 - Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nicht-toxischen salzen - Google Patents

Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nicht-toxischen salzen Download PDF

Info

Publication number: DD246298A5
Authority: DD; German Democratic Republic
Prior art keywords: acetoacetamide; methyl; dihydro; oxathiazin; dioxide
Prior art date: 1984-08-07

Application number

DD85279371A

Other languages

German (de)

English (en)

Inventor

Erwin Schmidt

Karl Clauss

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.)

1984-08-07

Filing date

1985-08-05

Publication date

1987-06-03

1985-08-05 Application filed by ��@��k�� filed Critical ��@��k��

1987-06-03 Publication of DD246298A5 publication Critical patent/DD246298A5/de

Links

150000003839 salts Chemical class 0.000 title claims abstract description 19
231100000252 nontoxic Toxicity 0.000 title claims abstract description 12
230000003000 nontoxic effect Effects 0.000 title claims abstract description 12
YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 title description 5
238000004519 manufacturing process Methods 0.000 title description 2
GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 claims abstract description 22
238000000034 method Methods 0.000 claims abstract description 21
150000001875 compounds Chemical class 0.000 claims abstract description 12
238000002360 preparation method Methods 0.000 claims abstract description 8
239000002585 base Substances 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
150000003512 tertiary amines Chemical class 0.000 claims description 6
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 5
150000004679 hydroxides Chemical class 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
239000003701 inert diluent Substances 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 4
150000002500 ions Chemical class 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 3
150000001342 alkaline earth metals Chemical class 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
235000013351 cheese Nutrition 0.000 claims 1
XLXCHZCQTCBUOX-UHFFFAOYSA-N 1-prop-2-enylimidazole Chemical compound C=CCN1C=CN=C1 XLXCHZCQTCBUOX-UHFFFAOYSA-N 0.000 abstract description 11
235000003599 food sweetener Nutrition 0.000 abstract description 4
239000003765 sweetening agent Substances 0.000 abstract description 4
239000000126 substance Substances 0.000 abstract description 3
235000013305 food Nutrition 0.000 abstract description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000460 chlorine Substances 0.000 description 8
WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 description 7
239000005935 Sulfuryl fluoride Substances 0.000 description 7
239000000619 acesulfame-K Substances 0.000 description 7
OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
RQIMPDXRFCFBGC-UHFFFAOYSA-N n-(oxomethylidene)sulfamoyl fluoride Chemical compound FS(=O)(=O)N=C=O RQIMPDXRFCFBGC-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000003085 diluting agent Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000002253 acid Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
-1 aliphatic halohydrocarbons Chemical class 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
229960005164 acesulfame Drugs 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 2
MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
239000003049 inorganic solvent Substances 0.000 description 2
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
XIMSTDAFGWROBF-UHFFFAOYSA-N oxathiazine 2-oxide Chemical compound O=S1OC=CC=N1 XIMSTDAFGWROBF-UHFFFAOYSA-N 0.000 description 2
IXPAAHZTOUOJJM-UHFFFAOYSA-N sulfuryl chloride fluoride Chemical compound FS(Cl)(=O)=O IXPAAHZTOUOJJM-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
SNDGLCYYBKJSOT-UHFFFAOYSA-N 1,1,3,3-tetrabutylurea Chemical compound CCCCN(CCCC)C(=O)N(CCCC)CCCC SNDGLCYYBKJSOT-UHFFFAOYSA-N 0.000 description 1
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 1
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 1
AXWKFRWLYPZEFQ-UHFFFAOYSA-N 3-oxobutanoyl chloride Chemical compound CC(=O)CC(Cl)=O AXWKFRWLYPZEFQ-UHFFFAOYSA-N 0.000 description 1
QXBGLCSYJYZBFK-UHFFFAOYSA-N 3-oxobutanoylsulfamic acid Chemical compound CC(=O)CC(=O)NS(O)(=O)=O QXBGLCSYJYZBFK-UHFFFAOYSA-N 0.000 description 1
HQTYWLJBELLQCX-UHFFFAOYSA-N 6-methyloxathiazin-4-one Chemical compound CC1=CC(=O)NSO1 HQTYWLJBELLQCX-UHFFFAOYSA-N 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
150000008043 acidic salts Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
239000012973 diazabicyclooctane Substances 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
239000003480 eluent Substances 0.000 description 1
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910001867 inorganic solvent Inorganic materials 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
229940017219 methyl propionate Drugs 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000003541 multi-stage reaction Methods 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QARNHIBOPBXNSX-UHFFFAOYSA-N prop-1-enoxymethylbenzene Chemical compound CC=COCC1=CC=CC=C1 QARNHIBOPBXNSX-UHFFFAOYSA-N 0.000 description 1
MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
- C07D291/02—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms not condensed with other rings
- C07D291/06—Six-membered rings

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Seasonings (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD85279371A 1984-08-07 1985-08-05 Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nicht-toxischen salzen DD246298A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19843429039 DE3429039A1 (de)	1984-08-07	1984-08-07	Verfahren zur herstellung von6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nichttoxischen salzen

Publications (1)

Publication Number	Publication Date
DD246298A5 true DD246298A5 (de)	1987-06-03

Family

ID=6242506

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD85279371A DD246298A5 (de)	1984-08-07	1985-08-05	Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nicht-toxischen salzen

Country Status (21)

Country	Link
US (1)	US4625024A (da)
EP (1)	EP0173082B1 (da)
JP (1)	JPS6147473A (da)
KR (1)	KR920008617B1 (da)
AR (1)	AR240454A1 (da)
AT (1)	ATE36851T1 (da)
AU (1)	AU575669B2 (da)
BR (1)	BR8503715A (da)
CA (1)	CA1241955A (da)
DD (1)	DD246298A5 (da)
DE (2)	DE3429039A1 (da)
DK (1)	DK167976B1 (da)
ES (1)	ES8604186A1 (da)
FI (1)	FI81790C (da)
HU (1)	HU197889B (da)
IE (1)	IE58482B1 (da)
IL (1)	IL76027A (da)
MX (1)	MX160726A (da)
NO (1)	NO163772C (da)
SU (1)	SU1491338A3 (da)
ZA (1)	ZA855921B (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3410439A1 (de) *	1984-03-22	1985-09-26	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nichttoxischen salzen sowie der dabei als zwischenprodukt(e) auftretenden acetoacetamind-n-sulfonsaeure(salze)
DE3410440A1 (de) *	1984-03-22	1985-09-26	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nichttoxischen salzen
LT3319949T (lt)	2016-09-21	2020-11-10	Celanese International Corporation	Kalio acesulfamo kompozicijos ir jų gamybos būdas
WO2018057387A1 (en)	2016-09-21	2018-03-29	Celanese International Corporation	Acesulfame potassium compositions and processes for producing same
HRP20201619T4 (hr)	2016-09-21	2025-03-28	Celanese International Corporation	Pripravci kalijevog acesulfama i postupci za njegovu proizvodnju
JP6818896B2 (ja)	2016-09-21	2021-01-27	セラニーズ・インターナショナル・コーポレーション	アセスルファムカリウム組成物及びその製造方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2001017C3 (de) *	1970-01-10	1978-05-18	Hoechst Ag, 6000 Frankfurt	3,4-Dihydro-1,23-oxathiazin-4on-2,2-dioxide, ihre Herstellung und Verwendung
DE2264235C3 (de) *	1972-12-30	1980-09-11	Hoechst Ag, 6000 Frankfurt	Verfahren zur Herstellung von 6-Methyl-3,4-dihydro-l,23-oxa thiazin-4-on-2,2-dioxid
DE2434548C2 (de) *	1974-07-18	1982-11-18	Hoechst Ag, 6000 Frankfurt	Verfahren zur Herstellung von Fluoridarmem 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid-kalium
DE2434549A1 (de) *	1974-07-18	1976-01-29	Hoechst Ag	Verfahren zur herstellung des suesstoffes 6-methyl-3,4-dihydro-1,2,3-oxathiazin4-on-2,2-dioxid
DE2447201A1 (de) *	1974-10-03	1976-04-08	Hoechst Ag	Verfahren zur herstellung von acetoacetamid-n-sulfofluorid
DE3410440A1 (de) *	1984-03-22	1985-09-26	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nichttoxischen salzen
DE3527070A1 (de) *	1985-07-29	1987-01-29	Hoechst Ag	Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid
DE3531358A1 (de) *	1985-09-03	1987-03-12	Hoechst Ag	Verfahren zur herstellung der nicht-toxischen salze des 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxids
DE3531359A1 (de) *	1985-09-03	1987-03-12	Hoechst Ag	Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid sowie zu dessen reinigung

1984
- 1984-08-07 DE DE19843429039 patent/DE3429039A1/de not_active Withdrawn
1985
- 1985-07-25 EP EP85109376A patent/EP0173082B1/de not_active Expired
- 1985-07-25 AT AT85109376T patent/ATE36851T1/de not_active IP Right Cessation
- 1985-07-25 DE DE8585109376T patent/DE3564682D1/de not_active Expired
- 1985-08-02 HU HU852963A patent/HU197889B/hu unknown
- 1985-08-05 AR AR301184A patent/AR240454A1/es active
- 1985-08-05 DD DD85279371A patent/DD246298A5/de not_active IP Right Cessation
- 1985-08-05 SU SU853933056A patent/SU1491338A3/ru active
- 1985-08-05 ES ES545878A patent/ES8604186A1/es not_active Expired
- 1985-08-05 FI FI853008A patent/FI81790C/fi not_active IP Right Cessation
- 1985-08-05 US US06/762,563 patent/US4625024A/en not_active Expired - Lifetime
- 1985-08-06 IE IE194085A patent/IE58482B1/en not_active IP Right Cessation
- 1985-08-06 ZA ZA855921A patent/ZA855921B/xx unknown
- 1985-08-06 AU AU45835/85A patent/AU575669B2/en not_active Expired
- 1985-08-06 DK DK358285A patent/DK167976B1/da not_active IP Right Cessation
- 1985-08-06 NO NO853103A patent/NO163772C/no unknown
- 1985-08-06 JP JP60171936A patent/JPS6147473A/ja active Granted
- 1985-08-06 BR BR8503715A patent/BR8503715A/pt unknown
- 1985-08-06 CA CA000488177A patent/CA1241955A/en not_active Expired
- 1985-08-06 IL IL76027A patent/IL76027A/xx not_active IP Right Cessation
- 1985-08-06 KR KR1019850005654A patent/KR920008617B1/ko not_active Expired
- 1985-08-07 MX MX206223A patent/MX160726A/es unknown

Also Published As

Publication number	Publication date
HUT39169A (en)	1986-08-28
DK167976B1 (da)	1994-01-10
FI81790B (fi)	1990-08-31
FI81790C (fi)	1990-12-10
ZA855921B (en)	1986-03-26
DK358285D0 (da)	1985-08-06
ES545878A0 (es)	1986-02-01
CA1241955A (en)	1988-09-13
ATE36851T1 (de)	1988-09-15
JPS6147473A (ja)	1986-03-07
US4625024A (en)	1986-11-25
HU197889B (en)	1989-06-28
AR240454A1 (es)	1990-04-30
IE58482B1 (en)	1993-09-22
ES8604186A1 (es)	1986-02-01
NO163772B (no)	1990-04-09
KR860001797A (ko)	1986-03-22
NO853103L (no)	1986-02-10
NO163772C (no)	1990-07-18
DE3429039A1 (de)	1986-02-20
IL76027A0 (en)	1985-12-31
FI853008L (fi)	1986-02-08
JPH0353306B2 (da)	1991-08-14
DE3564682D1 (en)	1988-10-06
MX160726A (es)	1990-04-27
EP0173082A1 (de)	1986-03-05
IE851940L (en)	1986-02-07
BR8503715A (pt)	1986-05-06
DK358285A (da)	1986-02-08
FI853008A0 (fi)	1985-08-05
EP0173082B1 (de)	1988-08-31
AU575669B2 (en)	1988-08-04
IL76027A (en)	1989-03-31
KR920008617B1 (ko)	1992-10-02
AU4583585A (en)	1986-02-13
SU1491338A3 (ru)	1989-06-30

Legal Events

Date	Code	Title	Description
2000-04-13	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD244554A5 (de)	1987-04-08	Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nicht-toxischen salzen
EP0215347B1 (de)	1990-01-24	Verfahren zur Herstellung von 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxid sowie zu dessen Reinigung
EP0217024B1 (de)	1990-04-25	Verfahren zur Herstellung von 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid
DE3531358A1 (de)	1987-03-12	Verfahren zur herstellung der nicht-toxischen salze des 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxids
EP0159516B1 (de)	1988-01-20	Verfahren zur Herstellung von 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nicht-toxischen Salzen
DD246298A5 (de)	1987-06-03	Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nicht-toxischen salzen
DE2354098B2 (de)	1976-05-13	Verfahren zur herstellung von mercaptocarbonsaeuren
EP0812821B1 (de)	2000-11-29	Kohlensäureesterbetaine und deren Herstellung und Verwendung
DE3531357A1 (de)	1987-03-12	Verfahren zur herstellung der nicht-toxischen salze des 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxids
DE3002553C2 (da)	1988-10-27
DE3044904A1 (de)	1982-07-01	Fluorierte anthranilsaeure und anthranilsaeurenitril sowie verfahren zu ihrer herstellung
AT352092B (de)	1979-08-27	Verfahren zur herstellung von acetoacetamid-n- sulfofluorid
DE2434562A1 (de)	1976-01-29	Verfahren zur herstellung des suessstoffes 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid
EP0571405A1 (de)	1993-12-01	Verfahren zur herstellung von 4-alkylsulfonyl-1-alkyl-2-chlorbenzolen und derartige verbindungen.
EP1204633B1 (de)	2004-02-18	Verfahren zur herstellung von 1-methyl-3-nitroguanidin
DE1568646B2 (de)	1974-09-05	Verfahren zur Herstellung von N-Hydroxyimidothi ocarbonsäureestera
DE2447201A1 (de)	1976-04-08	Verfahren zur herstellung von acetoacetamid-n-sulfofluorid
EP0482477A1 (de)	1992-04-29	Verfahren zur Herstellung von 6-Trifluormethyl-1,3,5-triazinen
DE2412578A1 (de)	1974-09-19	Verfahren zur herstellung substituierter aromatischer sulfone
DE2457032A1 (de)	1976-06-10	Verfahren zur herstellung von amidosulfonsaeurefluorid
DE2145308A1 (de)	1973-03-15	Verfahren zur herstellung von 4(4-hydroxyphenyl)-butan-2-on