DE97103C - - Google Patents
Info
- Publication number
- DE97103C DE97103C DENDAT97103D DE97103DA DE97103C DE 97103 C DE97103 C DE 97103C DE NDAT97103 D DENDAT97103 D DE NDAT97103D DE 97103D A DE97103D A DE 97103DA DE 97103 C DE97103 C DE 97103C
- Authority
- DE
- Germany
- Prior art keywords
- phenetidine
- acid ester
- anisidine
- orthoformic acid
- compound
- 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.)
- Active
Links
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 238000001311 chemical methods and process Methods 0.000 claims 1
- -1 orthoformic acid ester Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000155 melt Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 201000003152 motion sickness Diseases 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Patentirt im Deutschen Reiche vom 9. Juli 1897 ab.Patented in the German Empire on July 9, 1897.
Erhitzt man p-Phenetidin (34,6 kg) in alkoholischer Lösung während 10 Minuten mit 14,8 kg Orthoameisensa'ureester auf dem Wasserbade am Rückflufskühler und läfst das Reactionsproduct in verdünnte Natronlauge einlaufen, so scheidet sich ein OeI aus, welches nach kurzer Zeit erstarrt. Das Product wird mehrmals aus verdünntem Alkohol umkrystallisirt und schmilzt bei 1140; das Hydrochlorat schmilzt bei über 200°. Das Acetat ist in Wasser schwer löslich.If p-phenetidine (34.6 kg) is heated in alcoholic solution for 10 minutes with 14.8 kg of orthoformic acid ester on the water bath on the reflux condenser and the reaction product is run into dilute sodium hydroxide solution, an oil separates out, which after a short time stiffens. The product is several times recrystallized from dilute alcohol and melts at 114 0; the hydrochlorate melts at over 200 °. The acetate is sparingly soluble in water.
Für die Bereitung der Verbindung kann man auch direct Phenetidin und Orthoameisensäureester in neutraler Lösung erhitzen, jedoch ist die Ausbeute erheblich schlechter.Phenetidine and orthoformic acid ester can also be used for the preparation of the compound Heat in neutral solution, but the yield is considerably poorer.
Aus ρ-Anisidin und Orthoameisensäureester erhält man eine bei 119 ° schmelzende Verbindung: . ■■·■·.'·■'■■■■.A compound melting at 119 ° is obtained from ρ-anisidine and orthoformic acid ester: . ■■ · ■ ·. '· ■' ■■■■.
ZC6HtZC 6 Ht
.OC2H5 .OC 2 H 5
+ CHzOC2Hl: 5 ί ^OC2H,
■■■ ■ +3
'=CH
■ · I
JV ii + CHzOC 2 Hl: 5 ί ^ OC 2 H, ■■■ ■ +3 '= CH
■ · I
JV ii
OG2Ti5.OG 2 Ti 5 .
Analyse:Analysis:
Berechnet für: C11H20N2O2 Calculated for: C 11 H 20 N 2 O 2
C 71,83 pCt.
H 7,05 - '
N 9,85 - .C 71.83 pct.
H 7.05 - '
N 9.85 -.
Merkwürdigerweise gelingt es nicht, eine ähnliche Verbindung zu bereiten aus Orthoameisensäureester und ρ - Amidophenolhydrochlorat.. :Strangely enough, it is not possible to prepare a similar compound from orthoformic acid ester and ρ - amidophenol hydrochlorate ..:
Die Verbindung hat die Eigenschaft, die Haut unempfindlich zu machen, und in geringen Dosen hindert sie die Seekrankheit.The compound has the property of making the skin insensitive, and to a small extent Doses she prevents the seasickness.
Das Product unterscheidet sich von den Formylderivaten der Patentschrift Nr. 49075 Gefunden: C 71,49 pCt.The product differs from the formyl derivatives of Patent No. 49075 Found: C, 71.49 pCt.
H 7,3.: - H 7.3 .: -
N 9,65 -:. N 9.65 - :.
scharf durch seinen Schmelzpunkt und seine Zusammensetzung. , ■ ■'■.."'■ sharp by its melting point and its composition. , ■ ■ '■ .. "' ■
PatentiAnspruch:Patent claim:
Verfahren zur Darstellung von Methenyldip-phenetidin und -anisidin durch Condensation von p-Phenetidin und p-Anisidin mit Orthoameisensäureester. Process for the preparation of methenyldip-phenetidine and -anisidine by condensation of p-phenetidine and p-anisidine with orthoformic acid ester.
DERLlN. GEDRUCKT IN DER REICHSDRUCKEREI.DERLlN. PRINTED IN THE REICHSDRUCKEREI.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE97103C true DE97103C (en) |
Family
ID=368176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT97103D Active DE97103C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE97103C (en) |
-
0
- DE DENDAT97103D patent/DE97103C/de active Active
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