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Barbiturates 5-allyl

Allyl-5-(l-methylbutyl) barbituric acid (secobarbital Seconal)... [Pg.900]

Pd(Ph3P)4, 2-ethylhexanoic acid or barbituric acid (THF, 3 h, 93% yield). Tributylstannane can serve as an allyl scavenger. ... [Pg.410]

Preparation of 1-Methyl-5-Allyl-5-( 1-Methyl-2-Pentynyl) Barbituric Acid A solution of 23.8 g of sodium in 360 ml of absolute alcohol was prepared and thereto were added 38.3 g of methyl urea and 96.8 g of diethyl allyl (1-methyl-2-pentynyl) malonate. The mixture was refluxed for about 20 hours, cooled, and the ethanol was removed by distillation in vacuo. The residue was dissolved in about 300 ml of water and the aqueous solution was washed with ether, and the washings were discarded. The aqueous solution was then acidified with acetic acid, and extracted with three 150 ml of portions of ether. [Pg.983]

The combined ether extracts were washed with 5% aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, and fractionally distilled in vacuo. The fraction boiling at about 145° to 150°C at the pressure of 0.5 mm of mercury, weighing 61 g and consisting of 1-methyl-5-allyl-5-(1-methyl-2-pentynyl) barbituric acid, was collected. The only distillate was substantially pure, and could be used as such In pharmaceutical preparation or a salt could be prepared therefrom according to the procedures disclosed hereinafter. On standing, the oil crystallized. The crystalline 1-methyl-5-allyl-5-( 1-methyl-2-pentynyl) barbituric acid melted at about 60° to 64°C after recrystallization from dilute ethanol. [Pg.983]

Preparation of Sodium 1-Methyl-5-Allyl-5-(1-Methyl-2-Pentynyl) Barbiturate A solution of 61 g of 1-methyl-5-allyl-5-(1-methyl-2-pentynyl) barbituric acid in 100 ml of ether was extracted with 465 ml of 2% aqueous sodium hydroxide solution. The aqueous extract was washed with successive 75 ml and 50 ml portions of ether. The pH of the aqueous solution was adjusted to 11.7, using 5% aqueous sodium hydroxide solution. 5 g of decolorizing carbon were added to the solution with stirring the mixture was permitted to stand for 20 minutes at room temperature, and the carbon was removed by filtration. A solution containing 4 g of sodium carbonate in 25 ml of water was added to the aqueous solution, and the mixture was filtered sterile through a porcelain filter candle of 02 porosity into sterile bottles. The aqueous solution was then dried from the frozen state, whereupon a sterile residue of sodium 1-methyl-5-allyl-5-(1-methyl-2-pentynyl) barbiturate, weighing about 62 g was obtained. [Pg.983]

Parts of diallyl-barbituric acid are added to a precooled mixture of 1 5.5 parts of concentrated sulfuric acid and 0.5 part of water while stirring intensively, the mixture being cooled so that its temperature does not exceed 25°C. The honey-colored viscous solution Is stirred vigorously and all at once into 45 parts of water, whereupon the mixture warms up to 35°C to 40°C and, after several seconds, solidifies into a thick pulp, which Is then heated as quickly as possible to 95°C, at which temperature a clear solution Is formed. This is cooled slowly until the 5-allyl-5-((3-hydroxypropyl)-barbituric acid begins to form coarse-grained crystals, after which the mass is cooled rapidly to 20°C. [Pg.1327]

The thus-washed crude product is dissolved in a mixture of 12 parts of ethanol and 20 parts of benzene, with mild warming if necessary. 1 Part of sodium chloride and 1.5 parts of saturated aqueous sodium chloride solution are added to the obtained solution in ethanol-benzene, and whole thoroughly admixed. When the brine layer has settled. It is separated and the afore-described washing repeated. The clear solution is concentrated under reduced pressure until incipient formation of crystals and is then poured into 30 parts of benzene, whereupon a thick crystalline pulp is forthwith formed which, after being cooled to room temperature, is centrifuged off. The so-obtained 5-allyl-5-( 3-hydroxypropyl)-barbituric acid is dried at 70°C under reduced pressure and can be used for therapeutic purposes without further purification. Melting point 164 °C to 165°C. Yield 5 parts. [Pg.1327]

Propyl-methyl-carbiny I barbituric acid Allyl bromide Sodium hydroxide... [Pg.1370]

Propyl-methyl-carbinyl allyl barbituric acid (also called allyl 1-methyl-butyl barbituric acid) may be prepared as follows 1 mol of propyl-methyl-carbinyl barbituric acid is dissolved in a suitable vessel In a 10 to 35% aqueous solution of 1 mol of potassium hydroxide. To this are added somewhat in excess of 1 mol of allyl bromide, and alcohol equal to about 10% of the total volume of the solution. The vessel Is agitated for 50 to 75 hours. At the end of this time, the solution, which may still exhibit two layers, is concentrated to about one-half its volume to remove the excess allyl bromide and the alcohol. On cooling, an oily layer, which is propyl-methyl-carbinyl allyl barbituric acid, separates out as a sticky viscous mass. It is dried, washed with petroleum ether, and dissolved in the minimum amount of benzene. Any unreacted propyl-methyl-carbinyl barbituric acid, which does not dissolve, is filtered off. The addition of petroleum ether to the clear filtrate causes the propyl-methyl-carbinyl allyl barbituric acid to precipitate as an oily mass. [Pg.1370]

One part by weight of propyl-methyl-carbinyl allyl barbituric acid is added to enough alcohol to facilitate handling, in this case conveniently about six times its weight. To this is added a solution of sodium hydroxide, preferably carbonate-free or substantially so, containing °%38 parts by weight of sodium hydroxide, which is the amount of sodium hydroxide necessary to combine in equal molecular proportions with the propyl-methyl-carbinyl allyl barbituric acid. This solution is filtered clear, and is then evaporated under vacuum until the sodium propyl-methyl-carbinyl allyl barbiturate (alternatively named sodium allyl 1-methyl-butyl barbiturate) separates out in solid form. The salt as thus obtained in solid form contains a varying amount of moisture. [Pg.1370]

Sodium propyl-methyl-carbinyl allyl barbiturate is a white hygroscopic solid, readily soluble in water and alcohol, and insoluble In ether. [Pg.1370]

Synthesis of Immunogen (Hapten) The barbiturate, 5-ally 1-5-(1-carboxyisopropyl) barbituric acid (I) is first converted to 5-allyl-5-(1 -p-n i trophenyloxycarbonylisopropyl) barbituric acid (II) by the interaction of the base with /7-nitrophenol in N, N-dimethylformamide (DMF) as shown below ... [Pg.499]

A few barbiturates also contain an allylic group at C(5), e.g., allobarbi-tal (10.64, R = allyl), alphenal (10.64, R = Ph), aprobarbital (10.64, R = i-Pr), and secobarbital (10.64, R = 1-methylbutyl). These compounds were substrates of the epoxide-diol pathway in rats and guinea pigs. The relative... [Pg.642]

Secobarbital Secobarbital, 5-aUyl-5-(l-methylbutyl)barbituric acid (4.1.14), is also synthesized by the same standard schema of reacting a-allyl-a-(l-methylbutyl)-malonic ester with urea [14]. [Pg.62]

Cyclic thioureas such as 2-thiouracil 1118 (R = H), its 6-methyl 1118 (R = Me) and 6-propyl derivatives 1118 (R = Pr), as well as thiobarbital 1119 are effective agents against hyperthyroidism, while thiamylal 1120 is used as an anesthetic. A large number of barbituric acid derivatives have hypnotic or sedative effects, and allobarbital 1121 (R = R = allyl), aprobarbital 1121 (R = allyl, R = r-Pr), cyclobarbital 1121 (R = Et, R = 1-cyclohexenyl), pentobarbital 1121 (R = Et, R = 2-pentyl), phenobarbital 1121 (R = Et, R = Ph), propallyonal 1121 (R = isopropyl, R = 2-bromoallyl), and secobarbital 1121 (R = allyl, R = 2-pentyl) are all examples of N-unsubstituted barbiturates, while hexobarbital 1122 represents an N-methylated derivative. [Pg.243]

The most commonly used barbiturates are thiopentone [5-ethyl-5-(l-methylbutyl)-2-thiobarbituric acid], methohexitone [l-methyl-5-allyl-5-(l-methyl-2-pentynyl) barbituric acid], and thiamylal [5-allyl-5-(l-methylbutyl)-2-thio-barbituric acid]. Thiamylal is slightly more Table 4.3 Incidence of life-threatening hypersensitivity reactions to intravenous anaesthetic agents... [Pg.77]

The Pd(0)-catalyzed transfer of the allyl moiety to dimedone [23], morpholine [22], or N,N -dimethyl barbituric acid [27] resulted in the completely selective cleavage of the Aloe group, whereas the numerous other protecting groups and the glycosidic bonds,... [Pg.271]

The uses of constant-current coulometry for the determination of drugs in biological fluids are few, basically due to sensitivity restriction. Monforte and Purdy [46] have reported an assay for two allylic barbituric acid derivatives, sodium seconal and sodium sandoptal, with electrogenerated bromine as the titrant and biamperometry for endpoint detection. Quantitative bromination required an excess of bromine hence back titration with standard arsenite was performed. The assay required the formation of a protein-free filtrate of serum with tungstic acid, extraction into chloroform, and sample cleanup by back extraction, followed by coulometric titration with electrogenerated bromine. The protein precipitation step resulted in losses of compound due to coprecipitation. The recoveries of sodium seconal and sodium sandoptal carried through the serum assay were approximately 81 and 88%, respectively. Samples in the concentration range 7.5-50 pg/mL serum were analyzed by this procedure. [Pg.781]

BARBITURIC ACID, 5-ALLYL-5-(l-METHYLBUTYL)-2-THI0-, SODIUM SALT... [Pg.64]

The crystallized 5-allyl-5-(p-hydroxypropyl)-barbituric acid is centrifuged off,... [Pg.2905]

Allyl bromide Propyl-methyl-carbinyl barbituric acid... [Pg.3017]

Propyl-methyl-carbinyl allyl barbituric acid (also called allyl 1-methyl-butyl barbituric acid) may be prepared as follows 1 mol of propyl-methyl-carbinyl barbituric acid is dissolved in a suitable vessel in a 10 to 35% aqueous solution of 1 mol of potassium hydroxide. To this are added somewhat in excess of 1 mol of allyl bromide, and alcohol equal to about 10% of the total... [Pg.3017]


See other pages where Barbiturates 5-allyl is mentioned: [Pg.5391]    [Pg.382]    [Pg.852]    [Pg.531]    [Pg.150]    [Pg.86]    [Pg.1121]    [Pg.285]    [Pg.499]    [Pg.6]    [Pg.20]    [Pg.198]    [Pg.165]    [Pg.166]    [Pg.150]    [Pg.790]    [Pg.1393]    [Pg.745]    [Pg.2240]    [Pg.3018]   
See also in sourсe #XX -- [ Pg.625 ]




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5-Allyl-5- barbituric acid

Barbiturics

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