DE1903701A1 - Verfahren zur Herstellung von 1,2-Benzisoxazolen - Google Patents
Verfahren zur Herstellung von 1,2-BenzisoxazolenInfo
- Publication number
- DE1903701A1 DE1903701A1 DE19691903701 DE1903701A DE1903701A1 DE 1903701 A1 DE1903701 A1 DE 1903701A1 DE 19691903701 DE19691903701 DE 19691903701 DE 1903701 A DE1903701 A DE 1903701A DE 1903701 A1 DE1903701 A1 DE 1903701A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- benzisoxazole
- silica
- cleavage
- starting material
- 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 10
- 150000008316 benzisoxazoles Chemical class 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 29
- 238000003776 cleavage reaction Methods 0.000 claims description 12
- 230000007017 scission Effects 0.000 claims description 12
- 239000000377 silicon dioxide Substances 0.000 claims description 10
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000007858 starting material Substances 0.000 description 15
- 239000011148 porous material Substances 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- -1 salicylic acid nitrile Chemical class 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 235000019647 acidic taste Nutrition 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- XWQDMIXVAYAZGB-UHFFFAOYSA-N 5-chloro-2-hydroxybenzonitrile Chemical compound OC1=CC=C(Cl)C=C1C#N XWQDMIXVAYAZGB-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical compound CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 description 2
- PHZBRZBTCWCSLE-UHFFFAOYSA-N 5-chloro-3-methyl-1,2-benzoxazole Chemical compound C1=C(Cl)C=C2C(C)=NOC2=C1 PHZBRZBTCWCSLE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- VLXHAFNKABUTGH-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1.C1=CC=C2C=NOC2=C1 VLXHAFNKABUTGH-UHFFFAOYSA-N 0.000 description 1
- WZUODJNEIXSNEU-UHFFFAOYSA-N 2-Hydroxy-4-methoxybenzaldehyde Chemical class COC1=CC=C(C=O)C(O)=C1 WZUODJNEIXSNEU-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- XNPDLXPCYBWXFE-UHFFFAOYSA-N bis(2-hydroxy-1-phenylcyclohexyl)methanone Chemical compound OC1C(CCCC1)(C1=CC=CC=C1)C(=O)C1(C(CCCC1)O)C1=CC=CC=C1 XNPDLXPCYBWXFE-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 125000003544 oxime group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691903701 DE1903701A1 (de) | 1969-01-25 | 1969-01-25 | Verfahren zur Herstellung von 1,2-Benzisoxazolen |
| FR7001605A FR2029087A1 (en) | 1969-01-25 | 1970-01-16 | Process for 1,2-benzisoxazoles |
| BE744808D BE744808A (fr) | 1969-01-25 | 1970-01-22 | Procede de preparation de 1,2-benzisoxazoles |
| CH98770A CH515920A (de) | 1969-01-25 | 1970-01-23 | Verfahren zur Herstellung von 1,2-Benzisoxazolen |
| NL7000987A NL7000987A (fr) | 1969-01-25 | 1970-01-23 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691903701 DE1903701A1 (de) | 1969-01-25 | 1969-01-25 | Verfahren zur Herstellung von 1,2-Benzisoxazolen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1903701A1 true DE1903701A1 (de) | 1970-08-20 |
Family
ID=5723356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691903701 Pending DE1903701A1 (de) | 1969-01-25 | 1969-01-25 | Verfahren zur Herstellung von 1,2-Benzisoxazolen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE744808A (fr) |
| CH (1) | CH515920A (fr) |
| DE (1) | DE1903701A1 (fr) |
| FR (1) | FR2029087A1 (fr) |
| NL (1) | NL7000987A (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4452804A (en) * | 1981-02-25 | 1984-06-05 | Hoechst-Roussel Pharmaceuticals Inc. | 1,2-Benzisoxazoloxyethylamines and intermediates for the preparation thereof |
| US4504669A (en) * | 1981-02-25 | 1985-03-12 | Hoechst-Roussel Pharmaceuticals Inc. | 1,2-Benzisoxazoloxyethylamines and intermediates for the preparation thereof |
-
1969
- 1969-01-25 DE DE19691903701 patent/DE1903701A1/de active Pending
-
1970
- 1970-01-16 FR FR7001605A patent/FR2029087A1/fr not_active Withdrawn
- 1970-01-22 BE BE744808D patent/BE744808A/fr unknown
- 1970-01-23 CH CH98770A patent/CH515920A/de not_active IP Right Cessation
- 1970-01-23 NL NL7000987A patent/NL7000987A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE744808A (fr) | 1970-07-22 |
| NL7000987A (fr) | 1970-07-28 |
| CH515920A (de) | 1971-11-30 |
| FR2029087A1 (en) | 1970-10-16 |
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