US1036625A - Phenylethylcyanoacetic ester. - Google Patents

Phenylethylcyanoacetic ester. Download PDF

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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
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Prior art keywords
phenylethylcyanoacetic
ester
new
acid
esters
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US67447412A
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Heinrich Hoerlein
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Bayer AG
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Farbenfabriken Vorm Friedr Bayer and Co
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    • 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.

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.
US67447412A 1912-01-31 1912-01-31 Phenylethylcyanoacetic ester. Expired - Lifetime US1036625A (en)

Priority Applications (1)

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US67447412A US1036625A (en) 1912-01-31 1912-01-31 Phenylethylcyanoacetic ester.

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US67447412A US1036625A (en) 1912-01-31 1912-01-31 Phenylethylcyanoacetic ester.

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