Intravenous anesthetics of thiobarbital series. VI. Synthesis of sodium 5-allyl-5-isobutyl-2-thiobarbiturate was written by Abe, Kyuji;Matsui, Kazuo. And the article was included in Tanabe Seiyaku Kenkyu Nenpo in 1957.Related Products of 10203-58-4 This article mentions the following:
Na (11.5 g.) in 200 cc. EtOH is warmed with 80 g. CH2(CO2Et)2 at 40-50°, and the mixture treated with 102 g. iso-BuI over 4 hrs. to afford 74.5 g. di-Et isobutylmalonate (I), b7 95-8°. I (45 g.), 4.8 g. Na, and 150 cc. EtOH is warmed to 40-50°, 24.8 g. allyl bromide added over 1 hr., and the mixture boiled 3 hrs. to afford 45.6 g. di-Et isobutylallylmalonate (II), b7 114-16°. Isobutylation of di-Et allylmalonate also affords II in 81.9% yield. NCCH2CO2Et (57 g.) in a mixture of 11.5 g. Na and 300 cc. alc. treated with 102 g. iso-BuI affords 46.7 g. Et isobutylcyanoacetate (III), b9 93-7°. α-Chloroisocaproic acid (15 g.) in 50 cc. H2O is neutralized by NaHCO3, heated with 13 g. KCN, evaporated to dryness, a mixture of 26 cc. alc. and 20 cc. concentrated H2SO4 added, and the solution boiled 4 hrs. and distilled in vacuo to afford 7.5 g. III. III (42 g.), 5.7 g. Na, and 200 cc. EtOH is treated with 31 g. allyl bromide to afford 41.6 g. Et isobutylallylcyanoacetate (IV), b10 114-16°. IV (41.6 g.) and 30 g. thiourea in a mixture of 9.2 g. Na and 150 cc. EtOH boiled 6 hrs. and worked up gave 5-isobutyl-5-allyl-4-imino-2-thiobarbiturate (V), yellow, m. 276-8° (dioxane). V is boiled with 150 g. 30% H2SO4 to yield 24 g. 5-isobutyl-5-allyl-2-thiobarbiturate (VI), leaves, m. 145-7° (benzene). II (185 g.) and 110 g. thiourea boiled 7 hrs. with a mixture of 33.2 g. Na and 700 cc. MeOH yield VI. VI Na salt, a light yellow powder, is very hygroscopic and soluble in H2O, and useful as an ultra-short-acting intravenous anesthetic. In the experiment, the researchers used many compounds, for example, Diethyl isobutylmalonate (cas: 10203-58-4Related Products of 10203-58-4).
Diethyl isobutylmalonate (cas: 10203-58-4) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Related Products of 10203-58-4
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics