CH146430A - Process for the preparation of 4-amino-3,3'-dimethyl-diphenyl-cyclohexane-4'-oxamic acid. - Google Patents
Process for the preparation of 4-amino-3,3'-dimethyl-diphenyl-cyclohexane-4'-oxamic acid.Info
- Publication number
- CH146430A CH146430A CH146430DA CH146430A CH 146430 A CH146430 A CH 146430A CH 146430D A CH146430D A CH 146430DA CH 146430 A CH146430 A CH 146430A
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethyl
- cyclohexane
- amino
- diphenyl
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 159000000001 potassium salts Chemical class 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 3
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- PBNGGBIPMLBWCO-UHFFFAOYSA-N cyclohexane oxalic acid Chemical compound OC(=O)C(O)=O.C1CCCCC1 PBNGGBIPMLBWCO-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 4-Ämino-3.3'-diiiiethyl-diplienyl- cyclohexan-g-oxaminsäure. Vorliegendes Patent bezieht sich auf ein Verfahren zur Herstellung von 4-Amino-3.3'- dimethyl-diphetiyl-cyclohexan-4'- oxaminsäure, dadurch gekennzeichnet, dass man auf 4.4'- Diamino- <B>3.</B> ss'-dimethyl <B>-</B> diphenyl <B>-</B> cyclohexan Oxalsäure einwirken lässt.
Die erhaltene Monoxaminsäure ist ein fast weisses Pulver; sie liefert ein leicht lösliches Ammoniumsalz, dagegen schwer lösliche Na trium- und Kalitunsalze. Die aus Alkohol umkristallisierte Verbindung schmilzt bei ungefähr<B>216 0</B> unter Zersetzung.
<I>Beispiel:</I> 14,7<B>kg</B> 4. 4'-Diamitio-3. 3'-dimethyl-diphe- rjyl-1.1'-cyclohexan, erhalten durch Konden sation von-Cyclohexanon mit 2 Mol. o-Tolui- din, werden mit 4e0-Ute <U>r</U> Wasser und<B>16</B> kg kristallisierter Oxalsäure am Aus der anfänglich klaren Lösung scheidet sich die gebildete Oxaminsäure allmählich als schweres Pulver ab.
Wenn die -Menge nicht mehr zunimmt und d,e angewandte Base grösstenteils umgesetzt ist, wird der Niederschlag heiss abfiltriert und mit Wasser ge waschen. Zur Reinigung löst man ihn bei <B>60-70 0</B> in verdünntem Ainmontak, filtriert wenn nötig von geringen Mengen Vel#Llt)I#ei- nigungen ab und fällt aus dem Filtrat die freie Oxaminsäure warm init Säure aus.
Aus dem Filtrat kann man das nicht umgesetzte Ausgangsmaterial durch Zugabe von Animoniak abscheiden oder man kann das Filtrat unmittelbar zu einer neuen Um setzung verwenden.
Process for the preparation of 4-amino-3,3'-diiiiethyl-diplienyl-cyclohexane-g-oxamic acid. The present patent relates to a process for the preparation of 4-amino-3.3'-dimethyl-diphetiyl-cyclohexane-4'-oxamic acid, characterized in that one refers to 4.4'-diamino- <B> 3. </B> ss' -dimethyl <B> - </B> diphenyl <B> - </B> cyclohexane oxalic acid.
The monoxamic acid obtained is an almost white powder; it provides a readily soluble ammonium salt, whereas it provides poorly soluble sodium and potassium salts. The compound recrystallized from alcohol melts at approximately 216 ° with decomposition.
<I> Example: </I> 14.7 <B> kg </B> 4. 4'-Diamitio-3. 3'-dimethyl-dipherjyl-1.1'-cyclohexane, obtained by condensation of cyclohexanone with 2 moles of o-toluidine, are 4e0-ute <U> r </U> water and <B> 16 </B> kg of crystallized oxalic acid from the initially clear solution, the oxamic acid formed gradually separates out as a heavy powder.
When the amount no longer increases and the base used has largely reacted, the precipitate is filtered off while hot and washed with water. To clean it, it is dissolved at 60-70 ° in dilute aminmontak, if necessary small amounts of Vel # Llt) I # cleansings are filtered off and the free oxamic acid is precipitated from the filtrate warm with acid.
The unreacted starting material can be separated from the filtrate by adding anhydrous or the filtrate can be used directly for a new implementation.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE146430X | 1928-08-28 | ||
| CH144853T | 1929-08-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH146430A true CH146430A (en) | 1931-04-15 |
Family
ID=25714539
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH146430D CH146430A (en) | 1928-08-28 | 1929-08-22 | Process for the preparation of 4-amino-3,3'-dimethyl-diphenyl-cyclohexane-4'-oxamic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH146430A (en) |
-
1929
- 1929-08-22 CH CH146430D patent/CH146430A/en unknown
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