DE1153375B - Verfahren zur Herstellung von Benzoxazin-(1, 3)-dionen-(2, 4) - Google Patents
Verfahren zur Herstellung von Benzoxazin-(1, 3)-dionen-(2, 4)Info
- Publication number
- DE1153375B DE1153375B DET18445A DET0018445A DE1153375B DE 1153375 B DE1153375 B DE 1153375B DE T18445 A DET18445 A DE T18445A DE T0018445 A DET0018445 A DE T0018445A DE 1153375 B DE1153375 B DE 1153375B
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- acid
- given above
- binding agent
- dione
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 chlorocarbonic acid ester Chemical class 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 16
- 239000011230 binding agent Substances 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 7
- 230000002140 halogenating effect Effects 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- 239000012024 dehydrating agents Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- YSBUANSGDLZTKV-UHFFFAOYSA-N n-phenylcarbamoyl chloride Chemical compound ClC(=O)NC1=CC=CC=C1 YSBUANSGDLZTKV-UHFFFAOYSA-N 0.000 claims description 4
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 4
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 claims description 3
- DSUPUOGOCIFZBG-UHFFFAOYSA-N 2-(phenylcarbamoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=CC=CC=C1 DSUPUOGOCIFZBG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- CMEPUAROFJSGJN-UHFFFAOYSA-N 1,4-dioxan-2-ylmethanol Chemical compound OCC1COCCO1 CMEPUAROFJSGJN-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- NKBASRXWGAGQDP-UHFFFAOYSA-N 5-chlorosalicylic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1O NKBASRXWGAGQDP-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 150000007530 organic bases Chemical group 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 3
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 2
- UQRLKWGPEVNVHT-UHFFFAOYSA-N 3,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1 UQRLKWGPEVNVHT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 150000005130 benzoxazines Chemical class 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
- GUMCAKKKNKYFEB-UHFFFAOYSA-N 2,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1Cl GUMCAKKKNKYFEB-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- WWECJGLXBSQKRF-UHFFFAOYSA-N n,n-dimethylformamide;methanol Chemical compound OC.CN(C)C=O WWECJGLXBSQKRF-UHFFFAOYSA-N 0.000 description 1
- ZOCYRJKGMXEYTN-UHFFFAOYSA-N n-(4-chlorophenyl)carbamoyl chloride Chemical compound ClC(=O)NC1=CC=C(Cl)C=C1 ZOCYRJKGMXEYTN-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET18445A DE1153375B (de) | 1960-05-25 | 1960-05-25 | Verfahren zur Herstellung von Benzoxazin-(1, 3)-dionen-(2, 4) |
| CH1616765A CH412900A (de) | 1960-05-25 | 1961-05-04 | Verfahren zur Herstellung von neuen Benzo-1,3-oxazin-dionen-(2,4) |
| CH525861A CH411888A (de) | 1960-05-25 | 1961-05-04 | Verfahren zur Herstellung von neuen Benzo-1,3-oxazin-dionen-(2,4) |
| CH1616665A CH412899A (de) | 1960-05-25 | 1961-05-04 | Verfahren zur Herstellung von neuen Benzo-1,3-oxazin-dionen-(2,4) |
| FR862693A FR1148M (fr) | 1960-05-25 | 1961-05-24 | Benzo-1,3-oxazino-diones-(2,4). |
| BE604159A BE604159A (fr) | 1960-05-25 | 1961-05-24 | Procédé pour préparer des nouvelles benzo-1,3-oxazino-diones-(2,4) |
| GB18984/61A GB940164A (en) | 1960-05-25 | 1961-05-25 | Substituted benzo-1,3-oxazindiones-(2,4) |
| US282887A US3355453A (en) | 1960-05-25 | 1963-05-24 | Nu-substituted benzo-1, 3-oxazine-dione |
| NL6412458A NL6412458A (en:Method) | 1960-05-25 | 1964-10-26 | |
| NL6506352A NL6506352A (en:Method) | 1960-05-25 | 1965-05-19 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET18445A DE1153375B (de) | 1960-05-25 | 1960-05-25 | Verfahren zur Herstellung von Benzoxazin-(1, 3)-dionen-(2, 4) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1153375B true DE1153375B (de) | 1963-08-29 |
Family
ID=7548943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DET18445A Pending DE1153375B (de) | 1960-05-25 | 1960-05-25 | Verfahren zur Herstellung von Benzoxazin-(1, 3)-dionen-(2, 4) |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3355453A (en:Method) |
| BE (1) | BE604159A (en:Method) |
| CH (3) | CH411888A (en:Method) |
| DE (1) | DE1153375B (en:Method) |
| FR (1) | FR1148M (en:Method) |
| GB (1) | GB940164A (en:Method) |
| NL (2) | NL6412458A (en:Method) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3598814A (en) * | 1970-01-21 | 1971-08-10 | Carter Wallace | 3,3a-dihydro-2h,9h-isoxazolo(3,2-b)(1,3) benzoxazin-9-ones |
| US3684805A (en) * | 1969-03-24 | 1972-08-15 | Carter Wallace | 2,3,4,4a-TETRAHYDRO-10H-1,2-OXAZINO {8 3,2-b{9 (1,3)BENZOXAZIN-10-ONES |
| US3697517A (en) * | 1969-03-28 | 1972-10-10 | Bayer Ag | 1,3-benzoxazines |
| US3723426A (en) * | 1971-02-24 | 1973-03-27 | Ferro Corp | Benzoxazinediones |
| FR2434158A1 (fr) * | 1978-08-25 | 1980-03-21 | Esteve Int Prod | Nouveaux derives de 1,3-benzoxazine-2,4-dione, leur preparation et leur application en tant que medicaments |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2714105A (en) * | 1953-12-31 | 1955-07-26 | American Cyanamid Co | Benzoxazine diones and methods of preparing the same |
| US2776281A (en) * | 1956-01-30 | 1957-01-01 | American Cyanamid Co | Certain dihydro-benzoxazine-ones and dihydro benzothiazine-ones and process |
| US2806031A (en) * | 1956-04-30 | 1957-09-10 | Dow Chemical Co | 3, 4-dihydro-2h-1, 3-benzoxazines |
| US2811523A (en) * | 1956-03-02 | 1957-10-29 | Dow Chemical Co | 3, 4-dihydro-2h-1, 3-benzoxazines |
| US2825728A (en) * | 1956-12-12 | 1958-03-04 | Dow Chemical Co | Alkylene bis benzoxazine compounds |
| US2826576A (en) * | 1957-05-06 | 1958-03-11 | Dow Chemical Co | 3, 3' alkylenebis |
| US2826577A (en) * | 1957-05-06 | 1958-03-11 | Dow Chemical Co | Alkylenebis benzoxazines |
| US2835668A (en) * | 1956-06-22 | 1958-05-20 | Us Vitamin Corp | Pyridylethylated benzoxazinediones and process for preparation |
| AT201054B (de) * | 1953-08-05 | 1958-12-10 | Norwich Pharma Co | Verfahren zur Herstellung neuer Hydrazinoverbindungen der 5-Nitrofuran-Reihe |
| US2867618A (en) * | 1957-02-14 | 1959-01-06 | Dow Chemical Co | 3, 4-dihydro-2h-1, 3-benzoxazine |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL266824A (en:Method) * | 1960-07-15 | |||
| US3100174A (en) * | 1960-07-29 | 1963-08-06 | Pittsburgh Plate Glass Co | Preparation of wettable powders of 2-heptadecyl-2-imidazoline |
| US3122538A (en) * | 1961-11-14 | 1964-02-25 | Geigy Chem Corp | Pyrido-oxazine derivatives and a process for their preparation |
-
1960
- 1960-05-25 DE DET18445A patent/DE1153375B/de active Pending
-
1961
- 1961-05-04 CH CH525861A patent/CH411888A/de unknown
- 1961-05-04 CH CH1616665A patent/CH412899A/de unknown
- 1961-05-04 CH CH1616765A patent/CH412900A/de unknown
- 1961-05-24 BE BE604159A patent/BE604159A/fr unknown
- 1961-05-24 FR FR862693A patent/FR1148M/fr not_active Expired
- 1961-05-25 GB GB18984/61A patent/GB940164A/en not_active Expired
-
1963
- 1963-05-24 US US282887A patent/US3355453A/en not_active Expired - Lifetime
-
1964
- 1964-10-26 NL NL6412458A patent/NL6412458A/xx unknown
-
1965
- 1965-05-19 NL NL6506352A patent/NL6506352A/xx unknown
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT201054B (de) * | 1953-08-05 | 1958-12-10 | Norwich Pharma Co | Verfahren zur Herstellung neuer Hydrazinoverbindungen der 5-Nitrofuran-Reihe |
| US2714105A (en) * | 1953-12-31 | 1955-07-26 | American Cyanamid Co | Benzoxazine diones and methods of preparing the same |
| US2776281A (en) * | 1956-01-30 | 1957-01-01 | American Cyanamid Co | Certain dihydro-benzoxazine-ones and dihydro benzothiazine-ones and process |
| US2811523A (en) * | 1956-03-02 | 1957-10-29 | Dow Chemical Co | 3, 4-dihydro-2h-1, 3-benzoxazines |
| US2806031A (en) * | 1956-04-30 | 1957-09-10 | Dow Chemical Co | 3, 4-dihydro-2h-1, 3-benzoxazines |
| US2835668A (en) * | 1956-06-22 | 1958-05-20 | Us Vitamin Corp | Pyridylethylated benzoxazinediones and process for preparation |
| US2825728A (en) * | 1956-12-12 | 1958-03-04 | Dow Chemical Co | Alkylene bis benzoxazine compounds |
| US2867618A (en) * | 1957-02-14 | 1959-01-06 | Dow Chemical Co | 3, 4-dihydro-2h-1, 3-benzoxazine |
| US2826576A (en) * | 1957-05-06 | 1958-03-11 | Dow Chemical Co | 3, 3' alkylenebis |
| US2826577A (en) * | 1957-05-06 | 1958-03-11 | Dow Chemical Co | Alkylenebis benzoxazines |
Also Published As
| Publication number | Publication date |
|---|---|
| CH412899A (de) | 1966-05-15 |
| NL6412458A (en:Method) | 1964-12-28 |
| US3355453A (en) | 1967-11-28 |
| CH411888A (de) | 1966-04-30 |
| NL6506352A (en:Method) | 1965-07-26 |
| CH412900A (de) | 1966-05-15 |
| FR1148M (fr) | 1962-02-26 |
| BE604159A (fr) | 1961-11-24 |
| GB940164A (en) | 1963-10-23 |
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