CH140593A - Process for the preparation of a condensation product of the benzodiazine series. - Google Patents
Process for the preparation of a condensation product of the benzodiazine series.Info
- Publication number
- CH140593A CH140593A CH140593DA CH140593A CH 140593 A CH140593 A CH 140593A CH 140593D A CH140593D A CH 140593DA CH 140593 A CH140593 A CH 140593A
- Authority
- CH
- Switzerland
- Prior art keywords
- condensation product
- benzodiazine
- series
- preparation
- mol
- Prior art date
Links
- 239000007859 condensation product Substances 0.000 title claims description 6
- WCZVZNOTHYJIEI-UHFFFAOYSA-N Cinnoline Chemical class N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 229950000244 sulfanilic acid Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drugs Drugs 0.000 claims 1
- 239000000975 dye Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 1
- IGWIEYXEWVUGCK-UHFFFAOYSA-N 4-aminobenzenesulfonic acid;sodium Chemical compound [Na].NC1=CC=C(S(O)(=O)=O)C=C1 IGWIEYXEWVUGCK-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001809 detectable Effects 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Description
Verfahren zur Darstellung eines Kondensationsproduktes der Benzodiazinreihe. Gegenstand vorliegender Erfindung ist ein Verfahren zur Darstellung eines Kondensa tionsproduktes der Benzodiazinreihe, dadurch gekennzeichnet, dass man 1 Mol 2.4-Dihalo- genchinazolin mit 1 Mol 1-Aminobenzol-4- sulfosäure und 1 Mol 1-Amino-8-oxynaphtalin- 3.6-disulfosäure kondensiert.
<I>Beispiel:</I> Man tropft bei<B>50-600</B> zu einer Lösung von 19,5 Gewichtsteilen 1 - aminobenzol-4- sulfosaurem Natrium in 600 Gewichtsteilen Wasser, die mit 16,5 Gewichtsteilen Natrium acetat versetzt wurde, eine Lösung von 19,9 Gewichtsteilen 2,4-Dichlorchinazolin in der eben nötigen Menge Aceton langsam zu und hält die genannte Temperatur ein, bis die Reaktionskomponenten nicht mehr nachweis bar sind. Das auf diese Weise hergestellte, ausgesalzene Kondensationsprodukt der For mel
EMI0001.0018
bildet ein farbloses Pulver, das nicht mit salpeteriger Säure reagiert.
Diese Verbindung teigt man mit Wasser unter Zusatz von etwas Dioxan an und gibt den Teig langsam zu einer auf<B>90-1000</B> erwärmten Lösung von 36,3 Gewichtsteilen 1-amino-8-oxynaph- talin-3.6-disulfosaurem Natrium in 600 Ge wichtsteilen Wasser und 30 Teilen Kreide. Nach Beendigung der Kondensation fällt man durch Ansäuern.
Das Kondensationsprodukt hat die Formel:
EMI0002.0001
Nach der üblichen Aufarbeitung - Aussalzen aus einer heissen sodaalkalischen Lösung erhält man sein Natriumsalz als ein gelblich braun gefärbtes, in Blättchen kristallisieren des, in kaltem Wasser schwer lösliches Pul ver, welches auf Zusatz von Alkali leicht mit gelber Farbe in Lösung geht.
Process for the preparation of a condensation product of the benzodiazine series. The present invention is a process for the preparation of a condensation product of the benzodiazine series, characterized in that 1 mole of 2,4-dihalogenquinazoline with 1 mole of 1-aminobenzene-4-sulfonic acid and 1 mole of 1-amino-8-oxynaphthalene-3,6-disulfonic acid condensed.
<I> Example: </I> It is added dropwise at <B> 50-600 </B> to a solution of 19.5 parts by weight of sodium 1-aminobenzene-4-sulfonic acid in 600 parts by weight of water, which contains 16.5 parts by weight of sodium acetate was added, a solution of 19.9 parts by weight of 2,4-dichloroquinazoline in the just necessary amount of acetone slowly and maintains the temperature mentioned until the reaction components are no longer detectable. The salted out condensation product of the formula prepared in this way
EMI0001.0018
forms a colorless powder that does not react with nitric acid.
This compound is made into a paste with water with the addition of a little dioxane and the dough is slowly added to a solution, heated to 90-1000, of 36.3 parts by weight of 1-amino-8-oxynaphthalene-3,6-disulfonic acid Sodium in 600 parts by weight of water and 30 parts of chalk. After the condensation has ended, acidification is used to precipitate.
The condensation product has the formula:
EMI0002.0001
After the usual work-up - salting out a hot, soda-alkaline solution, its sodium salt is obtained as a yellowish brown colored, flaky powder, which is sparingly soluble in cold water and which easily dissolves with a yellow color when alkali is added.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE140593X | 1926-12-22 | ||
| CH133192T | 1927-12-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH140593A true CH140593A (en) | 1930-06-15 |
Family
ID=25712019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH140593D CH140593A (en) | 1926-12-22 | 1927-12-14 | Process for the preparation of a condensation product of the benzodiazine series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH140593A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1201844B (en) * | 1960-05-12 | 1965-09-30 | Mead Johnson & Co | Process for the preparation of 4-sulfanilamidoquinazoline derivatives substituted in the 2-position |
-
1927
- 1927-12-14 CH CH140593D patent/CH140593A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1201844B (en) * | 1960-05-12 | 1965-09-30 | Mead Johnson & Co | Process for the preparation of 4-sulfanilamidoquinazoline derivatives substituted in the 2-position |
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