DE2259329C2 - Verfahren zur Herstellung von Anthrachinonoxazolen - Google Patents
Verfahren zur Herstellung von AnthrachinonoxazolenInfo
- Publication number
- DE2259329C2 DE2259329C2 DE2259329A DE2259329A DE2259329C2 DE 2259329 C2 DE2259329 C2 DE 2259329C2 DE 2259329 A DE2259329 A DE 2259329A DE 2259329 A DE2259329 A DE 2259329A DE 2259329 C2 DE2259329 C2 DE 2259329C2
- Authority
- DE
- Germany
- Prior art keywords
- anthraquinone
- amino
- parts
- reaction
- oxazoles
- 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
- 238000000034 method Methods 0.000 title claims description 23
- BSXBWLBCNVXEQB-UHFFFAOYSA-N anthracene-9,10-dione;1,3-oxazole Chemical class C1=COC=N1.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 BSXBWLBCNVXEQB-UHFFFAOYSA-N 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000009833 condensation Methods 0.000 claims description 12
- 230000005494 condensation Effects 0.000 claims description 12
- -1 2-anthraquinonyl Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 150000004056 anthraquinones Chemical class 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 238000006798 ring closing metathesis reaction Methods 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- CLWMYQQCXBSIBF-UHFFFAOYSA-N 2-amino-3-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(N)C(Br)=C2 CLWMYQQCXBSIBF-UHFFFAOYSA-N 0.000 description 3
- VMOJFUJVEWWUAV-UHFFFAOYSA-N 2-amino-3-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(N)C(Cl)=C2 VMOJFUJVEWWUAV-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 description 3
- 150000001447 alkali salts Chemical class 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- CNWWMJSRHGXXAX-UHFFFAOYSA-N 2-amino-3-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(N)C(O)=C2 CNWWMJSRHGXXAX-UHFFFAOYSA-N 0.000 description 2
- POPBYCBXVLHSKO-UHFFFAOYSA-N 9,10-dioxoanthracene-1-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(=O)O POPBYCBXVLHSKO-UHFFFAOYSA-N 0.000 description 2
- ASDLSKCKYGVMAI-UHFFFAOYSA-N 9,10-dioxoanthracene-2-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 ASDLSKCKYGVMAI-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 150000000183 1,3-benzoxazoles Chemical class 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- BIZVHVKTTCPVPP-UHFFFAOYSA-N 1-amino-9,10-dioxoanthracene-2-carbonyl chloride Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(C(Cl)=O)=C2N BIZVHVKTTCPVPP-UHFFFAOYSA-N 0.000 description 1
- PMOCDYOEOUEPAN-UHFFFAOYSA-N 1-nitro-9,10-dioxoanthracene-2-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C(C(=O)O)=CC=C3C(=O)C2=C1 PMOCDYOEOUEPAN-UHFFFAOYSA-N 0.000 description 1
- CNRNYORZJGVOSY-UHFFFAOYSA-N 2,5-diphenyl-1,3-oxazole Chemical compound C=1N=C(C=2C=CC=CC=2)OC=1C1=CC=CC=C1 CNRNYORZJGVOSY-UHFFFAOYSA-N 0.000 description 1
- RHEVAQGXLUQWBM-UHFFFAOYSA-N 2-(1-amino-9,10-dioxoanthracen-2-yl)naphtho[2,3-f][1,3]benzoxazole-5,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C(C=C2O3)=C1C=C2N=C3C1=C(N)C(C(=O)C2=CC=CC=C2C2=O)=C2C=C1 RHEVAQGXLUQWBM-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- LLSVGXGSYBLMNY-UHFFFAOYSA-N 9,10-dioxoanthracene-1-carbonyl chloride Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(=O)Cl LLSVGXGSYBLMNY-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000005432 dialkylcarboxamide group Chemical group 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/32—1.3 azoles of the anthracene series
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)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2259329A DE2259329C2 (de) | 1972-12-04 | 1972-12-04 | Verfahren zur Herstellung von Anthrachinonoxazolen |
| CH1670273A CH588478A5 (en:Method) | 1972-12-04 | 1973-11-28 | |
| IT53987/73A IT1000169B (it) | 1972-12-04 | 1973-11-29 | Procedimento per la produzione di antrachinon ossazoli |
| US420702A US3926996A (en) | 1972-12-04 | 1973-11-30 | Production of anthraquinoneoxazoles |
| GB5591773A GB1445878A (en) | 1972-12-04 | 1973-12-03 | Production of anthraquinoneoxazoles |
| FR7342994A FR2208905B1 (en:Method) | 1972-12-04 | 1973-12-03 | |
| JP13494173A JPS5419891B2 (en:Method) | 1972-12-04 | 1973-12-04 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2259329A DE2259329C2 (de) | 1972-12-04 | 1972-12-04 | Verfahren zur Herstellung von Anthrachinonoxazolen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2259329A1 DE2259329A1 (de) | 1974-06-12 |
| DE2259329C2 true DE2259329C2 (de) | 1984-08-16 |
Family
ID=5863484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2259329A Expired DE2259329C2 (de) | 1972-12-04 | 1972-12-04 | Verfahren zur Herstellung von Anthrachinonoxazolen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3926996A (en:Method) |
| JP (1) | JPS5419891B2 (en:Method) |
| CH (1) | CH588478A5 (en:Method) |
| DE (1) | DE2259329C2 (en:Method) |
| FR (1) | FR2208905B1 (en:Method) |
| GB (1) | GB1445878A (en:Method) |
| IT (1) | IT1000169B (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4386206A (en) * | 1981-09-29 | 1983-05-31 | Dynapol | Tertiary amides as solvents in anthrapyridone syntheses |
| DE3903623A1 (de) * | 1989-02-08 | 1990-08-09 | Basf Ag | Verfahren zur herstellung von anthrachinonderivaten |
| US12047834B2 (en) | 2021-03-05 | 2024-07-23 | Comcast Cable Communications, Llc | Locating devices within a premises |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR941456A (fr) * | 1946-02-12 | 1949-01-12 | Ciba Geigy | Procédé de préparation de colorants de cuve de la série de l'anthraquinone, colorants de cuve conformes à ceux obtenus et emploi de ces colorants |
| US2683717A (en) * | 1950-12-30 | 1954-07-13 | Gen Aniline & Film Corp | Fluorescent vat dyestuffs |
| US2871240A (en) * | 1951-12-31 | 1959-01-27 | Gen Aniline & Film Corp | Dyestuffs derived from 2,5-dimethoxyterephthaloyl chloride and amino 1,9-anthrapyrimidine |
| CH429727A (de) * | 1961-06-17 | 1967-02-15 | Hodogaya Chemical Co Ltd | Verfahren zur Herstellung von a,B-Di(benzoxazolyl-(2))-äthylenen |
| CH452475A (de) * | 1965-05-20 | 1968-05-31 | Bayer Ag | Verfahren zum Färben und Bedrucken von synthetischem Textilmaterial mit Anthrachinonfarbstoffen |
| FR1498700A (en:Method) * | 1965-10-04 | 1968-01-10 | ||
| CH504505A (de) * | 1966-08-15 | 1971-03-15 | Ciba Geigy Ag | Verwendung von neuen Tolanderivaten als optische Aufhellmittel ausserhalb der Textilindustrie |
| DE1904433B2 (de) * | 1968-02-08 | 1977-11-03 | Ciba-Geigy Ag, Basel (Schweiz) | Kuepenfarbstoffe, verfahren zu deren herstellung und ihre verwendung |
-
1972
- 1972-12-04 DE DE2259329A patent/DE2259329C2/de not_active Expired
-
1973
- 1973-11-28 CH CH1670273A patent/CH588478A5/xx not_active IP Right Cessation
- 1973-11-29 IT IT53987/73A patent/IT1000169B/it active
- 1973-11-30 US US420702A patent/US3926996A/en not_active Expired - Lifetime
- 1973-12-03 GB GB5591773A patent/GB1445878A/en not_active Expired
- 1973-12-03 FR FR7342994A patent/FR2208905B1/fr not_active Expired
- 1973-12-04 JP JP13494173A patent/JPS5419891B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3926996A (en) | 1975-12-16 |
| CH588478A5 (en:Method) | 1977-06-15 |
| JPS4986363A (en:Method) | 1974-08-19 |
| FR2208905B1 (en:Method) | 1976-06-25 |
| DE2259329A1 (de) | 1974-06-12 |
| IT1000169B (it) | 1976-03-30 |
| GB1445878A (en) | 1976-08-11 |
| FR2208905A1 (en:Method) | 1974-06-28 |
| JPS5419891B2 (en:Method) | 1979-07-18 |
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| DE1142981B (de) | Verfahren zur Herstellung von Fluorubin |
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