2-(butoxymethyl)oxirane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 23.8 g (0.06 mol) of 2-(2,4-dihydroxyphenyl)-4,6-bis-(2,4-dimethylphenyl)-1,3,5-triazine (prepared as described in U.S. Pat. No. 3,244,708 Example 16) are suspended in 300 ml of xylene. 12.1 g (0.09 mol) of 97% butyl glycidyl ether and 0.75 g (0.006 mol) of dimethylbenzylamine are added to this suspension, and the mixture is heated to reflux temperature. After a reaction time of 5 hours the clear, brownish solution is cooled and clarified by filtration through 100 g of silica gel. The yellow solution is evaporated and the residue is recrystallized from hexane/toluene. This gives 27.3 g of pale yellow crystals of 2-[2-hydroxy-4(3-butoxy-2-hydroxypropyloxy)-phenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin (=86% yield). Melting point: 80-83° C. (Compound 1). the mixture is heated to reflux temperature After a reaction time of 5 hours the clear, brownish solution is cooled clarified by filtration through 100 g of silica gel The yellow solution is evaporated the residue is recrystallized from hexane/toluene

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

Procedure: Using the method of Example 15, supra, n-butyl glycidyl ether (143 μL, 1.0 mmol) and 1,1-dimethyl-2-(4-methoxyphenyl)ethylamine (197 mg, 1.1 mmol) were used to prepare 81 mg of the title compound as a clear, colorless oil: GC/EI-MS, m/z (rel. int.) 310 (M+1, 0.01), 174 (100), 163 (19), 132(18), 121(31), 70(20); 1H-NMR (CDCl3) δ 7.03 (2H, d, J=8.6), 6.87 (2H, d, J=8.6), 3.74 (1H, m), 3.72 (3H, s), 3.40 (4H, m), 2.73 (3H, m), 2.59 (3H, m), 1.50 (2H, m), 1.30 (2H, m), 1.01 (3H, s), 0.99 (3H, s), 0.87 (3H, t, J=7.4); 13C-NMR (CDCl3) δ 157.9, 131.2, 129.9, 113.2, 73.5, 71.2, 69.0, 54.9, 53.1, 46.2, 44.5, 31.5, 26.6, 26.4, 19.1, 13.8.

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

Procedure: If the butyl glycidyl ether is replaced by 2-ethylhexyl glycidyl ether, 2,4-di{2-hydroxy-4-[3-(2-ethylhexoxy)-2-hydroxypropoxy]phenyl}-6-methoxy-1,3,5-triazine having a melting point of 98°-99° C. is obtained. is obtained

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 5,5 dipropyl-(1H,3H,5H)-pyrimidine-2,4,6-trione (30.8 g, 0.15 mole) in dimethylformamide (30 ml) containing triethylamine (2.02 g, 0.2 mole) was mixed with butyl glycidyl ether (13 g, 0.1 mole). The mixture was heated at 60° C. for 6 hours. The solution was then diluted with water (150 ml) and extracted with toluene (2×50 ml). The organic layer was separated, washed with water (2×100 ml) dried and extracted with 5% aqueous sodium carbonate (6×100 ml). The toluene phase was then extracted with 1M aqueous sodium hydroxide (2×100 ml), the aqueous layers separated, washed with toluene (100 ml) and the pH was adjusted to 3 with sulphuric acid. The precipitated oily product was extracted with toluene (100 ml), and the organic layer was separated, washed with water, dried and evaporated to yield the title compound (16.3 g; 51.6%); purity by HPLC 96.5%. extracted with toluene (2×50 ml) The organic layer was separated washed with water (2×100 ml) dried extracted with 5% aqueous sodium carbonate (6×100 ml) The toluene phase was then extracted with 1M aqueous sodium hydroxide (2×100 ml) the aqueous layers separated washed with toluene (100 ml) The precipitated oily product was extracted with toluene (100 ml) the organic layer was separated washed with water dried evaporated

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 5,5 dipropyl-(1H,3H,5H)-pyrimidine-2,4,6-trione (30.8 g, 0.15 mole) in dimethylformamide (30 ml) containing triethylamine (2.02 g, 0.2 mole) was mixed with butyl glycidyl ether (13 g, 0.1 mole). The mixture was heated at 60° C. for 6 hours. The solution was then diluted with water (150 ml) and extracted with toluene (2×50 ml). The organic layer was separated, washed with water (2×100 ml) dried and extracted with 5% aqueous sodium carbonate (6×100 ml). The toluene phase was then extracted with 1M aqueous sodium hydroxide (2×100 ml), the aqueous layers separated, washed with toluene (100 ml) and the pH was adjusted to 3 with sulphuric acid. The precipitated oily product was extracted with toluene (100 ml), and the organic layer was separated, washed with water, dried and evaporated to yield the title compound (16.3 g; 51.6%); purity by HPLC 96.5%. extracted with toluene (2×50 ml) The organic layer was separated washed with water (2×100 ml) dried extracted with 5% aqueous sodium carbonate (6×100 ml) The toluene phase was then extracted with 1M aqueous sodium hydroxide (2×100 ml) the aqueous layers separated washed with toluene (100 ml) The precipitated oily product was extracted with toluene (100 ml) the organic layer was separated washed with water dried evaporated

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

Procedure: A solution of phenobarbital (69.6 g, 0.3 mole) in ethanol (150 ml) containing triethylamine (2.02 g, 0.02 mole) was stirred with butyl glycidyl ether (26.0 g, 0.2 mole) (available from Merck & Co.) for 6 hours at 70° C. The reaction mixture was then poured into water (500 ml) and the precipitated product was extracted with toluene (200 ml) at 70° C. The toluene layer was separated, washed with 3% aqueous sulphuric acid (200 ml) and left overnight at 4° C. The precipitated phenobarbital was filtered off and the filtrate extracted with 5% aqueous sodium carbonate (5×100 ml). The organic layer was then extracted with 1M aqueous sodium hydroxide (2×200 ml), the aqueous layers collected, washed with toluene (100 ml) and the pH was adjusted to 3 with sulphuric acid. The precipitated product was extracted with toluene (150 ml), the organic layer was separated, dried and evaporated under reduced pressure to give the title compound (40.1 g, 55%); purity by HPLC 99% m.p. 92° C. the precipitated product was extracted with toluene (200 ml) at 70° C The toluene layer was separated washed with 3% aqueous sulphuric acid (200 ml) The precipitated phenobarbital was filtered off the filtrate extracted with 5% aqueous sodium carbonate (5×100 ml) The organic layer was then extracted with 1M aqueous sodium hydroxide (2×200 ml) the aqueous layers collected washed with toluene (100 ml) The precipitated product was extracted with toluene (150 ml) the organic layer was separated dried evaporated under reduced pressure

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

Procedure: A solution of phenobarbital (69.6 g, 0.3 mole) in ethanol (150 ml) containing triethylamine (2.02 g, 0.02 mole) was stirred with butyl glycidyl ether (26.0 g, 0.2 mole) (available from Merck & Co.) for 6 hours at 70° C. The reaction mixture was then poured into water (500 ml) and the precipitated product was extracted with toluene (200 ml) at 70° C. The toluene layer was separated, washed with 3% aqueous sulphuric acid (200 ml) and left overnight at 4° C. The precipitated phenobarbital was filtered off and the filtrate extracted with 5% aqueous sodium carbonate (5×100 ml). The organic layer was then extracted with 1M aqueous sodium hydroxide (2×200 ml), the aqueous layers collected, washed with toluene (100 ml) and the pH was adjusted to 3 with sulphuric acid. The precipitated product was extracted with toluene (150 ml), the organic layer was separated, dried and evaporated under reduced pressure to give the title compound (40.1 g, 55%); purity by HPLC 99% m.p. 92° C. the precipitated product was extracted with toluene (200 ml) at 70° C The toluene layer was separated washed with 3% aqueous sulphuric acid (200 ml) The precipitated phenobarbital was filtered off the filtrate extracted with 5% aqueous sodium carbonate (5×100 ml) The organic layer was then extracted with 1M aqueous sodium hydroxide (2×200 ml) the aqueous layers collected washed with toluene (100 ml) The precipitated product was extracted with toluene (150 ml) the organic layer was separated dried evaporated under reduced pressure