GB814272A - 3,4-dihydro-2h-1,3-benzoxazines - Google Patents
3,4-dihydro-2h-1,3-benzoxazinesInfo
- Publication number
- GB814272A GB814272A GB2524757A GB2524757A GB814272A GB 814272 A GB814272 A GB 814272A GB 2524757 A GB2524757 A GB 2524757A GB 2524757 A GB2524757 A GB 2524757A GB 814272 A GB814272 A GB 814272A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dihydro
- benzoxazine
- dichlorophenyl
- cyclohexyl
- chloro
- 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.)
- Expired
Links
- WTAVYBAEMMFITK-UHFFFAOYSA-N 3,4-dihydro-2H-1,3-benzoxazine Chemical class C1=CC=C2OCNCC2=C1 WTAVYBAEMMFITK-UHFFFAOYSA-N 0.000 title abstract 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N Cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- PSOJLBXHRBFLLQ-UHFFFAOYSA-N 2-chloro-4,5-dimethylphenol Chemical compound CC1=CC(O)=C(Cl)C=C1C PSOJLBXHRBFLLQ-UHFFFAOYSA-N 0.000 abstract 2
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 abstract 2
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-Dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 abstract 1
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 abstract 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 abstract 1
- KEGTWUUHCSLGHJ-UHFFFAOYSA-N 6,8-dichloro-3-cyclohexyl-2,4-dihydro-1,3-benzoxazine Chemical compound C1C2=CC(Cl)=CC(Cl)=C2OCN1C1CCCCC1 KEGTWUUHCSLGHJ-UHFFFAOYSA-N 0.000 abstract 1
- FGVRQIQTCLJOFW-UHFFFAOYSA-N 6-chloro-3-cyclohexyl-2,4-dihydro-1,3-benzoxazine Chemical compound C1C2=CC(Cl)=CC=C2OCN1C1CCCCC1 FGVRQIQTCLJOFW-UHFFFAOYSA-N 0.000 abstract 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N Benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 1
- 101710016478 RNASEH2A Proteins 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000004188 dichlorophenyl group Chemical group 0.000 abstract 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229920002866 paraformaldehyde Polymers 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 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
- C07D265/16—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with only hydrogen or carbon atoms directly attached in positions 2 and 4
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)
Abstract
The invention comprises 3,4-dihydro-2H-1,3-benzoxazines of the general formula <FORM:0814272/IV (b)/1> (wherein R is cyclohexyl, benzyl or mono- or dichlorophenyl and n is 1 or 2), and their preparation by condensing an amine RNH2 with formaldehyde and reacting the product with the appropriate phenol derivative. In examples, m-chloroaniline is condensed with paraformaldehyde at 20-30 DEG C. in the presence of methanolic potassium hydroxide and the resulting solution is heated under reflux with p-chlorophenol to give 6 - chloro - 3 - (31 - chlorophenyl) - 3,4 - dihydro - 2H - 1,3 - benzoxazine; by replacing the m-chloroaniline with benzylamine. 3,4-dichloroaniline and cyclohexylamine, 3-benzyl-, 3 - (31,41 - dichlorophenyl) - and 3 - cyclohexyl-6 - chloro - 3,4 - dihydro - 2H - 1,3 - benzoxazine respectively are obtained; 3-cyclohexyl-6,8-dichloro - 3,4 - dihydro - 2H - 1,3 - benzoxazine is similarly prepared from cyclohexylamine, aqueous formaldehyde and 2,4-dichlorophenol. Other products obtainable by the same process are 6 - chloro - 3 - (21,41 - dichlorophenyl) - 3,4 - dihydro - 2H - 1,3 - benzoxazine and 3 - benzyl-and 3-(31-chlorophenyl)-6,8-dichloro-3,4-dihydro-2H-1, 3-benzoxazine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US568985A US2811523A (en) | 1956-03-02 | 1956-03-02 | 3, 4-dihydro-2h-1, 3-benzoxazines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB814272A true GB814272A (en) | 1959-06-03 |
Family
ID=1739068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2524757A Expired GB814272A (en) | 1956-03-02 | 1957-08-09 | 3,4-dihydro-2h-1,3-benzoxazines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB814272A (en) |
-
1957
- 1957-08-09 GB GB2524757A patent/GB814272A/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1035076A (en) | Improvements in or relating to the production of poly primary amines | |
| GB814272A (en) | 3,4-dihydro-2h-1,3-benzoxazines | |
| Lacey et al. | 437. Derivatives of acetoacetic acid. Part IX. The reaction of diketen with carbodi-imides | |
| FR908691A (en) | Process for the preparation of curable products, soluble in organic solvents, from condensation products of aminotriazines with formaldehyde | |
| GB863547A (en) | 3-mercapto-phenthiazine | |
| GB622955A (en) | Manufacture of ureas | |
| GB951887A (en) | Production of condensation products of vinylsulphonamide and formaldehyde | |
| GB989559A (en) | Polyamines | |
| GB634960A (en) | Methylolpentadecyl phenol and its derivatives | |
| SU62447A1 (en) | The method of obtaining NN'-di- (4-dibutylaminophenyl) -urea | |
| US2300678A (en) | N, n'-dimethylene-4, 4'-diaminodiphenyl sulphone | |
| GB1082017A (en) | Improvements in and relating to the preparation of n-(hydrocarbon substituted)-n-(1-alkenyl)-acetamides | |
| GB604675A (en) | Improvements in or relating substituted diamines | |
| GB690466A (en) | Derivatives of thiaxanthone | |
| GB676074A (en) | Manufacture of a new condensation product of sulphanilamidopyrimidine | |
| GB638534A (en) | Manufacture of new condensation products of sulphanilamidothiodiazoles | |
| FR885933A (en) | Process for the preparation of n, n'-disubstituted condensation products of the nature of urea | |
| FR1054177A (en) | Process for the production of ethers of condensation products of formaldehyde with amino-1, 3, 5-triazines containing at least two nh groups | |
| GB624380A (en) | Manufacture of a new condensation product of sulphathiazole | |
| GB716020A (en) | Improvements in the production of fungicidal cyclohexadienone derivatives | |
| GB677540A (en) | Improvements in or relating to the manufacture of benziminazoles | |
| GB720068A (en) | Production of modified melamine-formaldehyde resinous condensation products and mater ials treated therewith | |
| GB513113A (en) | Improvements in a process for producing resistant varnish coatings on wood | |
| GB723317A (en) | Di-alkyl substituted alkylene polyamino acetic acids | |
| GB549985A (en) | Improvements in or relating to the production of therapeutically-active derivatives of 4,4-diaminodiphenyl sulphone |