5,5-diethyl-1,3-diazinane-2,4,6-trione

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 18.4 g (0.1 mol) of 5,5-diethylbarbituric acid are reacted with 28.7 g (0.21 mol) of methyl γ-chlorobutyrate according to Example 1. 15.2 g (0.11 mol) of potassium carbonate powder are used as the acid acceptor and 100 ml of benzene and 100 ml of dimethylformamide are used as the solvent. The reaction is carried out exactly according to Example 1 and likewise worked up. In this manner, 38.3 g (99.7% of theory) of a clear, slightly discoloured viscous product are obtained. In this manner, 38.3 g (99.7% of theory) of a clear, slightly discoloured viscous product are obtained

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 40.7 g (0.7 mol) of propene oxide are added dropwise over the course of 1 hour to a mixture of 55.3 g of 5,5-diethylbarbituric acid (0.3 mol), 2.77 g of tetraethylammonium chloride (5 mol per cent) and 400 ml of dimethylformamide at 35° C. whilst stirring. Thereafter the mixture is gradually heated to 100° C. After 7 hours' stirring at 100° C. the mixture is worked-up in accordance with example 1. 92.5 g of crude 1,3-di(β-hydroxy-n-propyl)-5,5-diethylbarbituric acid (99.5 % of theory) are obtained. The product boils at 138°-148° C. under 0.08 mm Hg; 75.2 g of pure product 80% of theory) are obtained. After 7 hours' stirring at 100° C. the mixture

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 40.7 g (0.7 mol) of propene oxide are added dropwise over the course of 1 hour to a mixture of 55.3 g of 5,5-diethylbarbituric acid (0.3 mol), 2.77 g of tetraethylammonium chloride (5 mol per cent) and 400 ml of dimethylformamide at 35° C. whilst stirring. Thereafter the mixture is gradually heated to 100° C. After 7 hours' stirring at 100° C. the mixture is worked-up in accordance with example 1. 92.5 g of crude 1,3-di(β-hydroxy-n-propyl)-5,5-diethylbarbituric acid (99.5 % of theory) are obtained. The product boils at 138°-148° C. under 0.08 mm Hg; 75.2 g of pure product 80% of theory) are obtained. After 7 hours' stirring at 100° C. the mixture

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 40.7 g (0.7 mol) of propene oxide are added dropwise over the course of 1 hour to a mixture of 55.3 g of 5,5-diethylbarbituric acid (0.3 mol), 2.77 g of tetraethylammonium chloridde (5 mol percent) and 400 ml of dimethylformamide at 35° C. whilst stirring. Thereafter the mixture is gradually heated to 100° C. After 7 hours' stirring at 100° C. the mixture is worked-up in accordance with example 4. 92.5 g of crude 1,3-di(β-hydroxy-n-propyl)-5,5-diethylbarbituric acid (99.5% of theory) are obtained. The product boils at 138°-148° C. under 0.08 mm Hg; 75.2 g or pure product (80% of theory) are obtained. After 7 hours' stirring at 100° C. the mixture

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 46.05 g (0.25 mol) of diethylbarbituric acid, 96.9 g (0.525 mol) of 4-chloromethylbenzoic acid methyl ester and 38 g (0.275 mol) of finely ground, anhydrous potassium carbonate in 450 ml of dimethylformamide is stirred at room temperature and is heated to 100° C over the course of 2 hours. The reaction solution is kept at 100° C for one hour and the temperature is then raised to 135° C, whilst stirring. Stirring is continued for a further 4 hours at 135° C and the reaction mixture is then filtered, while still hot. 77.8 g of colourless crystals can be isolated from the cooled filtrate and concentrating the mother liquor gives a further 42 g of a syrup which crystallises (total yield of crude material: 119.8 g; theory: 120.1 g). is heated to 100° C over the course of 2 hours the temperature is then raised to 135° C whilst stirring Stirring is continued for a further 4 hours at 135° C the reaction mixture is then filtered

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 46.05 g (0.25 mol) of diethylbarbituric acid, 96.9 g (0.525 mol) of 4-chloromethylbenzoic acid methyl ester and 38 g (0.275 mol) of finely ground, anhydrous potassium carbonate in 450 ml of dimethylformamide is stirred at room temperature and is heated to 100° C over the course of 2 hours. The reaction solution is kept at 100° C for one hour and the temperature is then raised to 135° C, whilst stirring. Stirring is continued for a further 4 hours at 135° C and the reaction mixture is then filtered, while still hot. 77.8 g of colourless crystals can be isolated from the cooled filtrate and concentrating the mother liquor gives a further 42 g of a syrup which crystallises (total yield of crude material: 119.8 g; theory: 120.1 g). is heated to 100° C over the course of 2 hours the temperature is then raised to 135° C whilst stirring Stirring is continued for a further 4 hours at 135° C the reaction mixture is then filtered

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium Barbitone was made up to a final concentration of 0.07M together with 0.1% (w/v) sodium azide. The pH of this solution was adjusted to 8.4 with concentrated hydrochloric acid before making up to the final volume.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (41.2g sodium barbital in one liter of distilled water)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This example demonstrates the use of the method of the present invention in a T-4 test based on dilution of labeled T-4 added to a test sample. Two T-4 controls having assigned or known T-4 values were employed. Serum Sample 1 contained 9.2 μgm % T-4, while Serum Sample 2 contained 15.6 μgm % T-4. 0.1 ml of the serum samples was placed in separate test tubes. To each was added 1 ml of a phosphoric acid solution of calcium chloride containing 36 mg of calcium chloride/ml and having a pH of 1.5. Following mixing, there was added to each tube 0.1 ml of a solution having the following composition: 5 ml of barbital buffer of ionic strength, 0.075, 10 μl of 10% albumin and 5 μCi of I125 labeled T-4. The solution had a pH of approximately 8.6. The resulting solution was mixed and there was then added 2.5 ml of a barbital buffer of ionic strength, 0.075, having a pH of 8.6. Upon addition of the barbital buffer and mixing, there was formed a solid adsorbent comprised of calcium phosphate, the final mixture having a pH of approximately 5. The serum samples were centrifuged and the solid adsorbent in each case counted using a scintillation counter. The results are shown below: added to a test sample Following mixing The resulting solution was mixed mixing

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 18.4 g (0.1 mol) of 5,5-diethylbarbituric acid are reacted with 28.7 g (0.21 mol) of methyl γ-chlorobutyrate according to Example 1. 15.2 g (0.11 mol) of potassium carbonate powder are used as the acid acceptor and 100 ml of benzene and 100 ml of dimethylformamide are used as the solvent. The reaction is carried out exactly according to Example 1 and likewise worked up. In this manner, 38.3 g (99.7% of theory) of a clear, slightly discoloured viscous product are obtained. In this manner, 38.3 g (99.7% of theory) of a clear, slightly discoloured viscous product are obtained

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 40.7 g (0.7 mol) of propene oxide are added dropwise over the course of 1 hour to a mixture of 55.3 g of 5,5-diethylbarbituric acid (0.3 mol), 2.77 g of tetraethylammonium chloride (5 mol per cent) and 400 ml of dimethylformamide at 35° C. whilst stirring. Thereafter the mixture is gradually heated to 100° C. After 7 hours' stirring at 100° C. the mixture is worked-up in accordance with example 1. 92.5 g of crude 1,3-di(β-hydroxy-n-propyl)-5,5-diethylbarbituric acid (99.5 % of theory) are obtained. The product boils at 138°-148° C. under 0.08 mm Hg; 75.2 g of pure product 80% of theory) are obtained. After 7 hours' stirring at 100° C. the mixture

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 40.7 g (0.7 mol) of propene oxide are added dropwise over the course of 1 hour to a mixture of 55.3 g of 5,5-diethylbarbituric acid (0.3 mol), 2.77 g of tetraethylammonium chloridde (5 mol percent) and 400 ml of dimethylformamide at 35° C. whilst stirring. Thereafter the mixture is gradually heated to 100° C. After 7 hours' stirring at 100° C. the mixture is worked-up in accordance with example 4. 92.5 g of crude 1,3-di(β-hydroxy-n-propyl)-5,5-diethylbarbituric acid (99.5% of theory) are obtained. The product boils at 138°-148° C. under 0.08 mm Hg; 75.2 g or pure product (80% of theory) are obtained. After 7 hours' stirring at 100° C. the mixture