DE2651794C2 - Verfahren zur Herstellung von 5-Nitroso-2,4,6-triaminopyrimidin - Google Patents
Verfahren zur Herstellung von 5-Nitroso-2,4,6-triaminopyrimidinInfo
- Publication number
- DE2651794C2 DE2651794C2 DE2651794A DE2651794A DE2651794C2 DE 2651794 C2 DE2651794 C2 DE 2651794C2 DE 2651794 A DE2651794 A DE 2651794A DE 2651794 A DE2651794 A DE 2651794A DE 2651794 C2 DE2651794 C2 DE 2651794C2
- Authority
- DE
- Germany
- Prior art keywords
- nitroso
- reaction
- triaminopyrimidine
- mixture
- nitrosation
- 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 13
- XLQQJSWJHHKLOK-UHFFFAOYSA-N 5-nitrosopyrimidine-2,4,6-triamine Chemical compound NC1=NC(N)=C(N=O)C(N)=N1 XLQQJSWJHHKLOK-UHFFFAOYSA-N 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000543 intermediate Substances 0.000 claims description 4
- 230000009935 nitrosation Effects 0.000 claims description 4
- 238000007034 nitrosation reaction Methods 0.000 claims description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- NDEMNVPZDAFUKN-UHFFFAOYSA-N guanidine;nitric acid Chemical compound NC(N)=N.O[N+]([O-])=O.O[N+]([O-])=O NDEMNVPZDAFUKN-UHFFFAOYSA-N 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 238000010626 work up procedure Methods 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- -1 aliphatic Alcohols Chemical class 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 235000010288 sodium nitrite Nutrition 0.000 claims description 2
- 102100022404 E3 ubiquitin-protein ligase Midline-1 Human genes 0.000 claims 1
- 101710102210 E3 ubiquitin-protein ligase Midline-1 Proteins 0.000 claims 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 claims 1
- FNYLWPVRPXGIIP-UHFFFAOYSA-N Triamterene Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=CC=C1 FNYLWPVRPXGIIP-UHFFFAOYSA-N 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 239000007859 condensation product Substances 0.000 claims 1
- 239000000118 hair dye Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- PMBAJUMDARWMSF-UHFFFAOYSA-N 2-nitrosopropanedioic acid Chemical compound OC(=O)C(N=O)C(O)=O PMBAJUMDARWMSF-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229960004198 guanidine Drugs 0.000 description 1
- DXTIKTAIYCJTII-UHFFFAOYSA-N guanidine acetate Chemical compound CC([O-])=O.NC([NH3+])=N DXTIKTAIYCJTII-UHFFFAOYSA-N 0.000 description 1
- 229960000789 guanidine hydrochloride Drugs 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 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
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2651794A DE2651794C2 (de) | 1976-11-12 | 1976-11-12 | Verfahren zur Herstellung von 5-Nitroso-2,4,6-triaminopyrimidin |
| IT29470/77A IT1091568B (it) | 1976-11-12 | 1977-11-09 | Procedimento migliorato per la produzione di 5-nitroso-2,4,6-triammino-porimidina |
| FR7733990A FR2370738A1 (fr) | 1976-11-12 | 1977-11-10 | Procede perfectionne pour la preparation de la 5-nitroso-2,4,6-triaminopyrimidine par condensation du dinitrile malonique et de la guanidine |
| US05/850,287 US4145548A (en) | 1976-11-12 | 1977-11-10 | Method for the production of 5-nitroso-2,4,6-triaminopyrimidine |
| ES464062A ES464062A1 (es) | 1976-11-12 | 1977-11-11 | Procedimiento para la obtencion de 5-nitroso-2,4,6-triamino-pirimidina. |
| CH1380777A CH630616A5 (de) | 1976-11-12 | 1977-11-11 | Verfahren zur herstellung von 5-nitroso-2,4,6-triaminopyrimidin. |
| GB46958/77A GB1554095A (en) | 1976-11-12 | 1977-11-11 | Method of producing 5-nitroso-2,4,6-triaminopyrimidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2651794A DE2651794C2 (de) | 1976-11-12 | 1976-11-12 | Verfahren zur Herstellung von 5-Nitroso-2,4,6-triaminopyrimidin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2651794A1 DE2651794A1 (de) | 1978-05-18 |
| DE2651794C2 true DE2651794C2 (de) | 1982-09-23 |
Family
ID=5993069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2651794A Expired DE2651794C2 (de) | 1976-11-12 | 1976-11-12 | Verfahren zur Herstellung von 5-Nitroso-2,4,6-triaminopyrimidin |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4145548A (cg-RX-API-DMAC7.html) |
| CH (1) | CH630616A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2651794C2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES464062A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2370738A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1554095A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1091568B (cg-RX-API-DMAC7.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001089587A3 (de) * | 2000-05-19 | 2002-04-18 | Henkel Kgaa | Mittel zum färben von keratinhaltigen fasern |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH660589A5 (de) * | 1983-01-28 | 1987-05-15 | Lonza Ag | Verfahren zur herstellung von 2-substituierten 5-nitroso-4,6-diamino-pyrimidinen. |
| CH659248A5 (de) * | 1983-01-28 | 1987-01-15 | Lonza Ag | Verfahren zur herstellung von 2,4,5,6-tetraaminopyrimidin-sulfat. |
| US4831139A (en) * | 1983-01-28 | 1989-05-16 | Lonza Ltd. | Process for the preparation of 2-substituted 5-nitroso-4,6-diaminopyrimidines |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1364734A (fr) * | 1963-05-15 | 1964-06-26 | Lumiere Lab | Procédé de préparation de dérivés acyclique et cyclique de la guanidine |
-
1976
- 1976-11-12 DE DE2651794A patent/DE2651794C2/de not_active Expired
-
1977
- 1977-11-09 IT IT29470/77A patent/IT1091568B/it active
- 1977-11-10 FR FR7733990A patent/FR2370738A1/fr active Granted
- 1977-11-10 US US05/850,287 patent/US4145548A/en not_active Expired - Lifetime
- 1977-11-11 ES ES464062A patent/ES464062A1/es not_active Expired
- 1977-11-11 GB GB46958/77A patent/GB1554095A/en not_active Expired
- 1977-11-11 CH CH1380777A patent/CH630616A5/de not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001089587A3 (de) * | 2000-05-19 | 2002-04-18 | Henkel Kgaa | Mittel zum färben von keratinhaltigen fasern |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2370738B1 (cg-RX-API-DMAC7.html) | 1980-06-20 |
| IT1091568B (it) | 1985-07-06 |
| DE2651794A1 (de) | 1978-05-18 |
| CH630616A5 (de) | 1982-06-30 |
| ES464062A1 (es) | 1978-09-01 |
| US4145548A (en) | 1979-03-20 |
| GB1554095A (en) | 1979-10-17 |
| FR2370738A1 (fr) | 1978-06-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |