DE2016467C3 - Verfahren zur Herstellung von 1 -Hydroxy-6-nieder-alkoxy-phenazin-5,10-dioxiden - Google Patents
Verfahren zur Herstellung von 1 -Hydroxy-6-nieder-alkoxy-phenazin-5,10-dioxidenInfo
- Publication number
- DE2016467C3 DE2016467C3 DE2016467A DE2016467A DE2016467C3 DE 2016467 C3 DE2016467 C3 DE 2016467C3 DE 2016467 A DE2016467 A DE 2016467A DE 2016467 A DE2016467 A DE 2016467A DE 2016467 C3 DE2016467 C3 DE 2016467C3
- Authority
- DE
- Germany
- Prior art keywords
- iodinine
- reaction
- hydroxy
- hours
- dioxide
- 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 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 229940100198 alkylating agent Drugs 0.000 claims description 10
- 239000002168 alkylating agent Substances 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 150000004703 alkoxides Chemical class 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 5
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- NBMOVCYIGUDQJE-UHFFFAOYSA-N iodinin Chemical compound C1=CC=C2[N+]([O-])=C3C(O)=CC=CC3=[N+]([O-])C2=C1O NBMOVCYIGUDQJE-UHFFFAOYSA-N 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 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 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical group CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- -1 alkali metal salt Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- JIDVGUQUQSOHOL-UHFFFAOYSA-N myxin Chemical compound C1=CC=C2[N+]([O-])=C3C(OC)=CC=CC3=[N+]([O-])C2=C1O JIDVGUQUQSOHOL-UHFFFAOYSA-N 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 241000251748 Myxinidae Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- NNBFNNNWANBMTI-UHFFFAOYSA-M brilliant green Chemical compound OS([O-])(=O)=O.C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 NNBFNNNWANBMTI-UHFFFAOYSA-M 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81844869A | 1969-04-22 | 1969-04-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2016467A1 DE2016467A1 (de) | 1970-11-12 |
| DE2016467B2 DE2016467B2 (de) | 1979-05-10 |
| DE2016467C3 true DE2016467C3 (de) | 1980-01-24 |
Family
ID=25225563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2016467A Expired DE2016467C3 (de) | 1969-04-22 | 1970-04-08 | Verfahren zur Herstellung von 1 -Hydroxy-6-nieder-alkoxy-phenazin-5,10-dioxiden |
Country Status (13)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3681331A (en) * | 1970-04-02 | 1972-08-01 | Hoffmann La Roche | 1-hydroxy-6-amino alkoxy-phenazine 5,10-dioxides |
| GB201319363D0 (en) | 2013-11-01 | 2013-12-18 | Uni I Oslo | Compounds |
-
1970
- 1970-03-23 CH CH432670A patent/CH533628A/de not_active IP Right Cessation
- 1970-03-23 CH CH1728972A patent/CH546771A/xx not_active IP Right Cessation
- 1970-03-30 IL IL34193A patent/IL34193A0/xx unknown
- 1970-04-02 GB GB05635/70A patent/GB1260996A/en not_active Expired
- 1970-04-03 FI FI932/70A patent/FI54113C/fi active
- 1970-04-08 DE DE2016467A patent/DE2016467C3/de not_active Expired
- 1970-04-10 YU YU927/70A patent/YU34413B/xx unknown
- 1970-04-15 NL NL7005409A patent/NL7005409A/xx unknown
- 1970-04-20 IE IE498/70A patent/IE34101B1/xx unknown
- 1970-04-20 BE BE749172D patent/BE749172A/xx unknown
- 1970-04-21 AT AT216371A patent/AT299219B/de not_active IP Right Cessation
- 1970-04-21 AT AT360770A patent/AT295544B/de not_active IP Right Cessation
- 1970-04-21 FR FR707014385A patent/FR2060005B1/fr not_active Expired
- 1970-04-21 ES ES378852A patent/ES378852A1/es not_active Expired
- 1970-04-22 SE SE7005549A patent/SE376614B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH546771A (de) | 1974-03-15 |
| FR2060005A1 (enrdf_load_stackoverflow) | 1971-06-11 |
| CH533628A (de) | 1973-02-15 |
| SE376614B (enrdf_load_stackoverflow) | 1975-06-02 |
| FI54113B (fi) | 1978-06-30 |
| NL7005409A (enrdf_load_stackoverflow) | 1970-10-26 |
| IE34101L (en) | 1970-10-22 |
| BE749172A (fr) | 1970-10-20 |
| DE2016467A1 (de) | 1970-11-12 |
| AT295544B (de) | 1972-01-10 |
| AT299219B (de) | 1972-06-12 |
| GB1260996A (en) | 1972-01-19 |
| YU92770A (en) | 1978-12-31 |
| IE34101B1 (en) | 1975-02-05 |
| DE2016467B2 (de) | 1979-05-10 |
| YU34413B (en) | 1979-07-10 |
| IL34193A0 (en) | 1970-05-21 |
| FR2060005B1 (enrdf_load_stackoverflow) | 1973-03-16 |
| ES378852A1 (es) | 1973-01-16 |
| FI54113C (fi) | 1978-10-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |