CH289890A - A process for the preparation of an aromatic acylamidodiol. - Google Patents
A process for the preparation of an aromatic acylamidodiol.Info
- Publication number
- CH289890A CH289890A CH289890DA CH289890A CH 289890 A CH289890 A CH 289890A CH 289890D A CH289890D A CH 289890DA CH 289890 A CH289890 A CH 289890A
- Authority
- CH
- Switzerland
- Prior art keywords
- aromatic
- preparation
- partial hydrolysis
- acylamidodiol
- aminodiol
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and at least three atoms of bromine or iodine, bound to carbon atoms of the same non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Procédé de préparation d'un acylamidodiol aromatique. Dans le brevet. principal, on a décrit un procédé de préparation du P-1-phényl-2-a.cét- anûdopropane-1,3-diol.
Le présent. brevet. a pour objet un procédé de préparation d'un autre acylamidodiol aro matique.
Ce procédé est caractérisé en ce que l'on soumet à une hydrolyse partielle, dans des conditions aqueuses, la forme structurale pseudo d'un aminodiol triacylé de formule
EMI0001.0011
dans laquelle Ri et R3 sont des radicaux acyle, et dans des conditions telles qu'il se for=me le il'-1-p-iodophényl-2-dichloroacét- amidopropane-1,3-diol.
Ce composé est une nouvelle substance, laquelle est cristallisée et présente un point de fusion de 125-126 C (forme racémique).
De préférence, on effectue l'hydrolyse au moyen d'un hydroxyde d'un métal alcalin dissous dans une solution aqueuse contenant un solvant organique miscible avec l'eau. D'ordinaire, on soumet à ladite hydrolyse la forme racémique (dl) du P-1-p-iodophényl- 2-dichloroacétamido-1,3-diacétoxypropane. La température est avantageusement maintenue en dessous de 50 C et il est. préférable d'uti liser comme solvant organique miscible avec l'eau une cétone aliphatique telle que l'acétone ou un alcool miscible avec l'eau tel que l'alcool éthylique.
Les meilleurs résultats sont obtenus à, l'aide d'une solution aqueuse à 50% du sol vant organique miscible avec l'eau.
Le produit obtenu par le procédé selon l'invention est un produit intermédiaire pour la préparation de composés ayant une activité antibiotique et il présente lui-même une va leur thérapeutique. <I>Exemple:</I> On dissout, à une température de 0 C, 0,5 g de dl-P-1-p-iodophényl-2-dichloroacét- amido-1,3-diacétoxypropane dans un mélange composé de 30 cm3 d'acétone et d'un vohune égal d'une solution 0,2 n de NaOH. On laisse reposer le mélange réactionnel pendant une heure,
on le neutralise ensuite avec de l'acide sulfurique et on l'évapore à siccité sous pres sion réduite. On extrait plusieurs fois le résidu avec de l'acétate d'éthyle; après réunion de ces extraits à l'acétate d'éthyle, on les sèche et l'acétate d'éthyle est distillé dans le vide pour obtenir le dl-!U-1-p-iodophényl-2-dichloroaeét- amidopropane-1,3-diol de point de fusion 125 à 126 C.
Process for preparing an aromatic acylamidodiol. In the patent. Mainly, a process for the preparation of P-1-phenyl-2-a.cet-anudopropane-1,3-diol has been described.
The present. patent. relates to a process for preparing another aromatic acylamidodiol.
This process is characterized in that the pseudo structural form of a triacylated aminodiol of formula is subjected to partial hydrolysis, under aqueous conditions.
EMI0001.0011
wherein R 1 and R 3 are acyl radicals, and under conditions such that il'-1-p-iodophenyl-2-dichloroacet-amidopropane-1,3-diol is formed.
This compound is a new substance, which crystallizes and has a melting point of 125-126 C (racemic form).
Preferably, the hydrolysis is carried out by means of an alkali metal hydroxide dissolved in an aqueous solution containing an organic solvent miscible with water. Usually, the racemic form (dl) of P-1-p-iodophenyl-2-dichloroacetamido-1,3-diacetoxypropane is subjected to said hydrolysis. The temperature is advantageously kept below 50 C and it is. It is preferable to use as the water-miscible organic solvent an aliphatic ketone such as acetone or a water-miscible alcohol such as ethyl alcohol.
The best results are obtained with the aid of a 50% aqueous solution of the organic soil miscible with water.
The product obtained by the process according to the invention is an intermediate product for the preparation of compounds having antibiotic activity and it itself has a therapeutic value. <I> Example: </I> 0.5 g of dl-P-1-p-iodophenyl-2-dichloroacét-amido-1,3-diacetoxypropane is dissolved at a temperature of 0 C in a mixture composed of 30 cm3 of acetone and an equal volume of 0.2 n NaOH solution. The reaction mixture is left to stand for one hour,
it is then neutralized with sulfuric acid and evaporated to dryness under reduced pressure. The residue is extracted several times with ethyl acetate; after combining these extracts with ethyl acetate, they are dried and the ethyl acetate is distilled in vacuo to obtain dl-! U-1-p-iodophenyl-2-dichloroaeet-amidopropane-1, 3-diol melting point 125-126 C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US289890XA | 1948-03-16 | 1948-03-16 | |
| CH283750T | 1948-12-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH289890A true CH289890A (en) | 1953-03-31 |
Family
ID=25732284
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH289890D CH289890A (en) | 1948-03-16 | 1948-12-15 | A process for the preparation of an aromatic acylamidodiol. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH289890A (en) |
-
1948
- 1948-12-15 CH CH289890D patent/CH289890A/en unknown
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