DE1302657B - - Google Patents
Info
- Publication number
- DE1302657B DE1302657B DENDAT1302657D DE1302657DA DE1302657B DE 1302657 B DE1302657 B DE 1302657B DE NDAT1302657 D DENDAT1302657 D DE NDAT1302657D DE 1302657D A DE1302657D A DE 1302657DA DE 1302657 B DE1302657 B DE 1302657B
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- ester
- general formula
- mol
- cyanate
- 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
- -1 phenoxyphenyl Chemical group 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 10
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000002329 infrared spectrum Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- HUUFTQGAUDUEBG-UHFFFAOYSA-N ethyl 4-cyanatobenzoate Chemical compound CCOC(=O)C1=CC=C(OC#N)C=C1 HUUFTQGAUDUEBG-UHFFFAOYSA-N 0.000 claims 1
- 229940102398 methyl anthranilate Drugs 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 7
- CWHFDTWZHFRTAB-UHFFFAOYSA-N phenyl cyanate Chemical compound N#COC1=CC=CC=C1 CWHFDTWZHFRTAB-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 229960001047 methyl salicylate Drugs 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BAQGCWNPCFABAY-UHFFFAOYSA-N methyl 2-sulfanylbenzoate Chemical compound COC(=O)C1=CC=CC=C1S BAQGCWNPCFABAY-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BRBXNVQANQPNPP-UHFFFAOYSA-N (2,4-dichlorophenyl) cyanate Chemical compound ClC1=CC=C(OC#N)C(Cl)=C1 BRBXNVQANQPNPP-UHFFFAOYSA-N 0.000 description 1
- JRBJLOCMQWBLDF-UHFFFAOYSA-N (2,6-dichlorophenyl) cyanate Chemical compound ClC1=CC=CC(Cl)=C1OC#N JRBJLOCMQWBLDF-UHFFFAOYSA-N 0.000 description 1
- GYIUFGWIHNSVCN-UHFFFAOYSA-N (2-chlorophenyl) cyanate Chemical compound ClC1=CC=CC=C1OC#N GYIUFGWIHNSVCN-UHFFFAOYSA-N 0.000 description 1
- GWBSCOKVLHUIHQ-UHFFFAOYSA-N (2-methylphenyl) cyanate Chemical compound CC1=CC=CC=C1OC#N GWBSCOKVLHUIHQ-UHFFFAOYSA-N 0.000 description 1
- SHBUQGBESNZMCH-UHFFFAOYSA-N (2-nitrophenyl) cyanate Chemical class [O-][N+](=O)C1=CC=CC=C1OC#N SHBUQGBESNZMCH-UHFFFAOYSA-N 0.000 description 1
- MHPDOOHLJBFGCC-UHFFFAOYSA-N (2-phenoxyphenyl) cyanate Chemical class N#COC1=CC=CC=C1OC1=CC=CC=C1 MHPDOOHLJBFGCC-UHFFFAOYSA-N 0.000 description 1
- SZYHWJHZQIMXKD-UHFFFAOYSA-N 2,2,2-tribromoethyl cyanate Chemical compound BrC(COC#N)(Br)Br SZYHWJHZQIMXKD-UHFFFAOYSA-N 0.000 description 1
- JYUYGTBHNYYSQG-UHFFFAOYSA-N 2,2-dichloroethyl cyanate Chemical compound ClC(Cl)COC#N JYUYGTBHNYYSQG-UHFFFAOYSA-N 0.000 description 1
- UYDGECQHZQNTQS-UHFFFAOYSA-N 2-amino-4,6-dimethylpyridine-3-carboxamide Chemical compound CC1=CC(C)=C(C(N)=O)C(N)=N1 UYDGECQHZQNTQS-UHFFFAOYSA-N 0.000 description 1
- AUZQQIPZESHNMG-UHFFFAOYSA-N 3-methoxysalicylic acid Chemical class COC1=CC=CC(C(O)=O)=C1O AUZQQIPZESHNMG-UHFFFAOYSA-N 0.000 description 1
- NJESAXZANHETJV-UHFFFAOYSA-N 4-methylsalicylic acid Chemical compound CC1=CC=C(C(O)=O)C(O)=C1 NJESAXZANHETJV-UHFFFAOYSA-N 0.000 description 1
- XAICWTLLSRXZPB-UHFFFAOYSA-N 5-tert-butyl-2-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC=C(O)C(C(O)=O)=C1 XAICWTLLSRXZPB-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- GYCKQBWUSACYIF-UHFFFAOYSA-N Ethyl salicylate Chemical compound CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
- VLMOSYXUVIVLAZ-UHFFFAOYSA-N N#CO.C1=CC=C2N=CC=CC2=C1 Chemical class N#CO.C1=CC=C2N=CC=CC2=C1 VLMOSYXUVIVLAZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- CAIKKJIIZHDMSX-UHFFFAOYSA-N ethyl 2-sulfanylbenzoate Chemical compound CCOC(=O)C1=CC=CC=C1S CAIKKJIIZHDMSX-UHFFFAOYSA-N 0.000 description 1
- ATMSMRINTOGATK-UHFFFAOYSA-N ethyl 5-chloro-2-hydroxybenzoate Chemical compound CCOC(=O)C1=CC(Cl)=CC=C1O ATMSMRINTOGATK-UHFFFAOYSA-N 0.000 description 1
- 229940005667 ethyl salicylate Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- SUHLUMKZPUMAFP-UHFFFAOYSA-N methyl 2-hydroxy-3-methylbenzoate Chemical compound COC(=O)C1=CC=CC(C)=C1O SUHLUMKZPUMAFP-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- QUSFOLYSOPZYIK-UHFFFAOYSA-N naphthalen-1-yl cyanate Chemical compound C1=CC=C2C(OC#N)=CC=CC2=C1 QUSFOLYSOPZYIK-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- WHSXTWFYRGOBGO-UHFFFAOYSA-N o-cresotic acid Natural products CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- USOBLRADELOQLD-UHFFFAOYSA-N phenyl 2-cyanatobenzoate Chemical compound C=1C=CC=C(OC#N)C=1C(=O)OC1=CC=CC=C1 USOBLRADELOQLD-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1302657B true DE1302657B (enrdf_load_stackoverflow) | 1970-11-26 |
Family
ID=621393
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1302657D Pending DE1302657B (enrdf_load_stackoverflow) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1302657B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0245902A3 (en) * | 1986-05-13 | 1989-02-15 | Shell Internationale Researchmaatschappij B.V. | Benzothiazinone derivatives |
-
0
- DE DENDAT1302657D patent/DE1302657B/de active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0245902A3 (en) * | 1986-05-13 | 1989-02-15 | Shell Internationale Researchmaatschappij B.V. | Benzothiazinone derivatives |
| US4833137A (en) * | 1986-05-13 | 1989-05-23 | Shell Internationale Research Maatschappij B.V. | Benzothiazinone derivatives |
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