US1036625A - Phenylethylcyanoacetic ester. - Google Patents
Phenylethylcyanoacetic ester. Download PDFInfo
- Publication number
- US1036625A US1036625A US67447412A US1912674474A US1036625A US 1036625 A US1036625 A US 1036625A US 67447412 A US67447412 A US 67447412A US 1912674474 A US1912674474 A US 1912674474A US 1036625 A US1036625 A US 1036625A
- Authority
- US
- United States
- Prior art keywords
- phenylethylcyanoacetic
- ester
- new
- acid
- esters
- 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 - Lifetime
Links
- 150000002148 esters Chemical class 0.000 title description 9
- 239000000203 mixture Substances 0.000 description 4
- IUZIGXNXWJEZLU-UHFFFAOYSA-N 2-(2-phenylethyl)propanedioic acid Chemical compound OC(=O)C(C(O)=O)CCC1=CC=CC=C1 IUZIGXNXWJEZLU-UHFFFAOYSA-N 0.000 description 3
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- CZZKRHOLRJNATP-UHFFFAOYSA-N ethyl 2-cyano-4-phenylbutanoate Chemical compound CCOC(=O)C(C#N)CCC1=CC=CC=C1 CZZKRHOLRJNATP-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 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 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000007656 barbituric acids Chemical class 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000019248 orcein Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Definitions
- phenylethylcyano-acetic esters can be obtained by treating the phenylcyano-acetic esters with ethylbromid.
- the new esters are valuable intermediate products for the production of substituted barbituricacids' which are valuable therapeutic compounds.
- caustic alkali Upon treatment with caustic alkali they are split up into alcohols and a mixture of phenylethylmalonic acid and phenylethylacetic acid.
- esters of the present invention have the following formula:
- the resulting mixture is then heated to boiling in a vessel provided with a reflux condenser until the liquid shows a neutral reaction to lacmus.
- the liquid is filtered, the alcohol is distilled off and the ester is isolated in the usual way.
- the new phenylethylcyanoacetic ethyl ester is a limpid oil boiling at 155 C. under a pressure of 18 mm.
- phenylethylcyanoacetic esters being liquids which are splitup by the action of caustic alkali into alcohols and a mixture of phenylethylmalonic acid with phenylethylacetic acid, substantially as described.
- the phenylethylcyanoacetic ethyl ester being a limpid oilboiling at 155 .C. under a pressure of 18 mm. and split up by the action of caustic alkali into alcohol and a mixture of phenylethylmalonic acid and phenylethylacetic acid, substantially as described.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
HEINRICH HfiRLEIN, OF VOHWINKEL, NEAR ELBERFELD, GERMANY, ASSIGNOR TO FARBENFABRIKEN VORM. FRIEDR. BAYER & 00., OF ELBERFELD, GERMANY, A
conronnrion or GERMANY.
PHENYLETHYLCYANOAGETIC ESTER.
No Drawing.
Patented Aug. 27, 1912.
To all whom it may concern:
Be it known that I, HEINRICH HoRLEIN, doctor of philosophy, chemist, citizen of the German Empire, residing at Vohwinkel, near Elberfeld, Germany, have invented new and useful Improvementsin Phenylethylcyanoacetic Ester, of which the'following is a specification.
I have found that the hitherto unknown phenylethylcyano-acetic esters can be obtained by treating the phenylcyano-acetic esters with ethylbromid. The new esters are valuable intermediate products for the production of substituted barbituricacids' which are valuable therapeutic compounds. Upon treatment with caustic alkali they are split up into alcohols and a mixture of phenylethylmalonic acid and phenylethylacetic acid.
The esters of the present invention have the following formula:
0255 \\COOR (R=alkyl, aralkyl, aryl).
In order to illustrate the new process more fully the following example is given, the
7 parts being by weight :'189 parts of phenylare added to a solution of 23 parts of sodium in 300 parts of alcohol (free from water).
The resulting mixture is then heated to boiling in a vessel provided with a reflux condenser until the liquid shows a neutral reaction to lacmus. The liquid is filtered, the alcohol is distilled off and the ester is isolated in the usual way. The new phenylethylcyanoacetic ethyl ester is a limpid oil boiling at 155 C. under a pressure of 18 mm.
1- claim 1. As new products, the phenylethylcyanoacetic esters being liquids which are splitup by the action of caustic alkali into alcohols and a mixture of phenylethylmalonic acid with phenylethylacetic acid, substantially as described.
2. As a new product, the phenylethylcyanoacetic ethyl ester, being a limpid oilboiling at 155 .C. under a pressure of 18 mm. and split up by the action of caustic alkali into alcohol and a mixture of phenylethylmalonic acid and phenylethylacetic acid, substantially as described.
In testimony whereof I have hereunto set my hand in the presence of two subscribing witnesses.
HEINRICH HORLEIN. [1,. 8.
Witnesses HELEN NUFER, A. NUFER.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67447412A US1036625A (en) | 1912-01-31 | 1912-01-31 | Phenylethylcyanoacetic ester. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67447412A US1036625A (en) | 1912-01-31 | 1912-01-31 | Phenylethylcyanoacetic ester. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1036625A true US1036625A (en) | 1912-08-27 |
Family
ID=3104904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US67447412A Expired - Lifetime US1036625A (en) | 1912-01-31 | 1912-01-31 | Phenylethylcyanoacetic ester. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1036625A (en) |
-
1912
- 1912-01-31 US US67447412A patent/US1036625A/en not_active Expired - Lifetime
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