5.5- Diallylbarbituric acid

Therapeutic Function Sedative, Hypnotic Chemical Name Barbituric acid, 5,5-diallyl-Common Name Diallylbarbituric acid, Allobarbital, Diallymal Structural Formula ... 

To a mixture of 43 parts barbituric acid, 200 parts of water and 5 parts of cuprous sulfate in 10 parts of water is added 82 parts of allylbromide. Then at room temperature is added 27 parts of sodium hydroxide (10% aqueous solution). 5,5-Diallylbarbituric acid is isolated by filtration. After recrystallization from water 5,5-diallylbarbituric acid has melting polint 169-170°C. 

Proprietary Name. It is an ingredient of Dialog. 5,5-Diallylbarbituric acid... 

The TV-carboxymethyl derivatives of barbituric acid can be obtained by condensation of barbiturate with appropriate chloroesters.273 Similarly, N-substituted barbiturates containing a basic group at the nitrogen atom were formed. Treatment of 5,5-dialkylbarbituric acid with benzylaminoethyl chloride in the presence of sodium ethanolate led to JV-(2 -benzylaminoethyl)-5,5-diallylbarbituric acid.274... 

Rautio.295-297 Four main products of reduction were isolated for each barbiturate (112 R1 = Me, Et R2 = Ph R1 = R2 = allyl R3 = H, Me), namely, di- and tetrahydrobarbiturates 113 and 114 when one or two carbonyl groups were reduced to a secondary hydroxyl group, primary alcohols 115, which were formed via the reductive cleavage of the barbituric acid ring, and urea derivatives 116, which were formed simultaneously with the primary alcohols from the rest of the ring298 (Scheme 8). Additionally, the reduction of l-methyl-5,5-diallylbarbituric acid led to formation of small amounts of 117.299... 

Hydrolysis was the accompanying reaction to the reduction of 5,5-diallylbarbituric acid with NaBH4309,364 and to the N-methylation of different barbiturates.363-367 The effects of different protecting agents and solubilizers on the stability of medicinal barbiturates also deserve close attention because of their pharmaceutical importance.335,368-375 The stability of barbiturates in frozen systems has also been investigated.327 376 377... 

Fw. 33. Gas chromatogram of a standard mixture of nine barbiturates. Two micrograms of each barbiturate was injected in 4 /d of CHClj. For column preparation see text. Column temperature programmed from 160° at 4° per minute. Attenuation X 160. A = Barbital B = diallylbarbituric acid C = butethal D = amobar-bital E = pentobarbital F = secobarbital G = hexobarbital H = cyclobarbital I = heptabarbital. F. M. Model 810 gas chromatograph. 

Phenols, such as e-nitrophenol (cf. Acetophenetidine), are alkylated by heating with alkyl chlorides in the presence of aqueous alkali. Methyl and ethyl bromides or iodides react very smoothly and, in spite of their cost, find application iii the field of dyes and medicinal products, e.g., pyramidone and antipyrine, for the preparation of simple and mixed ethers and for the alkylation of phenols and amines. Allyl bromide is employed for making diallylbarbituric acid (Dial). 

Diallylbarbituric acid 2,4, 6 (IH, 3H, 5H)-Pyrimidinetrione, 5,5-di-2-propenyl- Allobarbital Diallylbarbitone Diallylmalonylurea Diallymalum Allobarbitone (BPC 1959)... 

Sandberg F. Anesthetic properties of some new N-substituted and N,N -disubstituted derivatives of 5,5-diallylbarbituric acid. Acta Physiol Scand 1951 24 7-26. 

Fig. 4. The chemical grovps in diallylbarbituric acid and in DDC that can induce...

The reaction of two derivatives of 5,5-diallylbarbituric acid with sulphuric acid in acetonitrile is said to give characterizable 6-sultones. Addition of SO3 to hexafluorobutadiene occurs in a 1,2 manner to give (128). The double bond of (128) can be brominated to give another stable -sultone. The addition is reversible above 20 °C, and (128) reacts with excess SO3 to give (129) and SOj. ... 

The three effective compounds AIA, Sedormid, and diallylbarbituric acid all possess allyl groups, a tertiary carbon atom, and an acid amide group (S80). Their similarity to pyrimidine is noteworthy (Fig, 30). McLennan and Elliott (384) suggest that barbiturates interfere with the synthe of acetylcholine. 

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