AT215993B - Verfahren zur Herstellung von neuen 4-Oxo-2-(halogenalkyl)-2,3-dihydro-[benzo-1,3-oxazinen] - Google Patents
Verfahren zur Herstellung von neuen 4-Oxo-2-(halogenalkyl)-2,3-dihydro-[benzo-1,3-oxazinen]Info
- Publication number
- AT215993B AT215993B AT522258A AT522258A AT215993B AT 215993 B AT215993 B AT 215993B AT 522258 A AT522258 A AT 522258A AT 522258 A AT522258 A AT 522258A AT 215993 B AT215993 B AT 215993B
- Authority
- AT
- Austria
- Prior art keywords
- water
- salicylamide
- chloroform
- aldehyde
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 title description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 55
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 51
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 38
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims description 26
- 229960000581 salicylamide Drugs 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 18
- 238000009833 condensation Methods 0.000 claims description 15
- 230000005494 condensation Effects 0.000 claims description 15
- 229960000583 acetic acid Drugs 0.000 claims description 14
- 239000007789 gas Substances 0.000 claims description 14
- 239000012362 glacial acetic acid Substances 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 11
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 11
- 239000012433 hydrogen halide Substances 0.000 claims description 11
- 239000002244 precipitate Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 238000010533 azeotropic distillation Methods 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 3
- 238000012986 modification Methods 0.000 claims 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 238000011065 in-situ storage Methods 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound 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 claims 1
- 238000010626 work up procedure Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 58
- 239000000203 mixture Substances 0.000 description 15
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 14
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 6
- -1 halogenated aliphatic aldehydes Chemical class 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 5
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 5
- MRMOPHYFXXZTFN-UHFFFAOYSA-N 5-bromo-2-hydroxybenzamide Chemical compound NC(=O)C1=CC(Br)=CC=C1O MRMOPHYFXXZTFN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 150000001241 acetals Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- NNHMQZBVJPQCAK-UHFFFAOYSA-N 5-chloro-2-hydroxybenzamide Chemical compound NC(=O)C1=CC(Cl)=CC=C1O NNHMQZBVJPQCAK-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- OMAKZNALRADTRX-UHFFFAOYSA-N 1,1,3-trimethoxybutane Chemical compound COC(C)CC(OC)OC OMAKZNALRADTRX-UHFFFAOYSA-N 0.000 description 1
- CERVLVANLTVGSM-UHFFFAOYSA-N 2-methoxybutanal Chemical compound CCC(OC)C=O CERVLVANLTVGSM-UHFFFAOYSA-N 0.000 description 1
- VVXNMKJDQVBOLT-UHFFFAOYSA-N 3-methoxybutanal Chemical compound COC(C)CC=O VVXNMKJDQVBOLT-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- 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
- C07D265/20—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 position 4
- C07D265/22—Oxygen atoms
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET13932A DE1167839B (de) | 1957-07-27 | 1957-07-27 | Verfahren zur Herstellung von 4-Oxo-2-(halogenalkyl)-2, 3-dihydro-benzoxazinen-(1, 3) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT215993B true AT215993B (de) | 1961-07-10 |
Family
ID=7547493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT522258A AT215993B (de) | 1957-07-27 | 1958-07-23 | Verfahren zur Herstellung von neuen 4-Oxo-2-(halogenalkyl)-2,3-dihydro-[benzo-1,3-oxazinen] |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT215993B (fr) |
| BE (1) | BE569839R (fr) |
| CH (1) | CH365076A (fr) |
| DE (1) | DE1167839B (fr) |
| GB (1) | GB869093A (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1185619B (de) * | 1961-11-14 | 1965-01-21 | Geigy Ag J R | Verfahren zur Herstellung von neuen Pyrido[2, 3-e] [1, 3]-oxazinen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE959825C (de) * | 1955-04-28 | 1957-03-14 | Thomae Gmbh Dr K | Verfahren zur Herstellung von in 2-Stellung endocyclisch substituierten 2, 3-Dihydro-enzo-1, 3-oxazonen-(4) |
-
1957
- 1957-07-27 DE DET13932A patent/DE1167839B/de active Pending
-
1958
- 1958-07-10 CH CH6158358A patent/CH365076A/de unknown
- 1958-07-23 AT AT522258A patent/AT215993B/de active
- 1958-07-28 BE BE569839A patent/BE569839R/fr active
- 1958-07-28 GB GB24261/58A patent/GB869093A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1185619B (de) * | 1961-11-14 | 1965-01-21 | Geigy Ag J R | Verfahren zur Herstellung von neuen Pyrido[2, 3-e] [1, 3]-oxazinen |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1167839B (de) | 1964-04-16 |
| BE569839R (fr) | 1961-06-30 |
| CH365076A (de) | 1962-10-31 |
| GB869093A (en) | 1961-05-31 |
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