1-(2,6-dimethylphenyl)-3-ethylthiourea

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Oxalyl chloride (7.62 g; 0.06 mol) was added dropwise to the stirring solution of N-(2,6-dimethylphenyl)-N′-ethylthiourea (10.4 g; 0.05 mol) in methylene chloride (200 mL). The mixture was heated at reflux for 1 hour then evaporated to dryness. Ethanol (100 mL) was added and the mixture was heated at reflux for 1 hour then evaporated to dryness. The residue was dissolved in ethyl acetate (300 mL) and washed with 2N hydrochloric acid (500 mL) then with water (300 mL). The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was crystallized from ether/hexane to give 6.0 g of 1-(2,6-Dimethylphenyl)-3-ethyl-2-thioxo-4,5-imidazolidinedione, m.p. 103–105° C. Mass spectrum; FAB (M+H)+ m/z 263. 1H-NMR (DMSO-d6; 300 MHz): δ 7.31–7.27 (m, 1H), 7.18 (d, 2H), 3.94 (q, 2H), 2.08 (s, 6H), and 1.25 ppm (t, 3H). The mixture was heated at reflux for 1 hour then evaporated to dryness Ethanol (100 mL) was added the mixture was heated at reflux for 1 hour then evaporated to dryness The residue was dissolved in ethyl acetate (300 mL) washed with 2N hydrochloric acid (500 mL) The organic phase was dried over anhydrous magnesium sulfate evaporated to dryness The residue was crystallized from ether/hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Oxalyl chloride (7.62 g; 0.06 mol) was added dropwise to the stirring solution of N-(2,6-dimethylphenyl)-N′-ethylthiourea (10.4 g; 0.05 mol) in methylene chloride (200 mL). The mixture was heated at reflux for 1 hour then evaporated to dryness. Ethanol (100 mL) was added and the mixture was heated at reflux for 1 hour then evaporated to dryness. The residue was dissolved in ethyl acetate (300 mL) and washed with 2N hydrochloric acid (500 mL) then with water (300 mL). The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was crystallized from ether/hexane to give 6.0 g of 1-(2,6-Dimethylphenyl)-3-ethyl-2-thioxo-4,5-imidazolidinedione, m.p. 103–105° C. Mass spectrum; FAB (M+H)+ m/z 263. 1H-NMR (DMSO-d6; 300 MHz): δ 7.31–7.27 (m, 1H), 7.18 (d, 2H), 3.94 (q, 2H), 2.08 (s, 6H), and 1.25 ppm (t, 3H). The mixture was heated at reflux for 1 hour then evaporated to dryness Ethanol (100 mL) was added the mixture was heated at reflux for 1 hour then evaporated to dryness The residue was dissolved in ethyl acetate (300 mL) washed with 2N hydrochloric acid (500 mL) The organic phase was dried over anhydrous magnesium sulfate evaporated to dryness The residue was crystallized from ether/hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2,6-Dimethylphenyl isothiocyanate (16.3 g; 0.1 mol) was added dropwise to 110 mL of 70% aqueous ethylamine solution. The mixture was stirred for 1 hour at ambient temperature. Excess ethylamine was evaporated under a stream of nitrogen. The mixture was diluted with water (100 mL). The solid was collected by filtration and washed with water and dried to give 20.0 g of N-(2,6-dimethylphenyl)-N′-ethylthiourea. Excess ethylamine was evaporated under a stream of nitrogen The mixture was diluted with water (100 mL) The solid was collected by filtration washed with water dried

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Oxalyl chloride (7.62 g; 0.06 mol) was added dropwise to the stirring solution of N-(2,6-dimethylphenyl)-N′-ethylthiourea (10.4 g; 0.05 mol) in methylene chloride (200 mL). The mixture was heated at reflux for 1 hour then evaporated to dryness. Ethanol (100 mL) was added and the mixture was heated at reflux for 1 hour then evaporated to dryness. The residue was dissolved in ethyl acetate (300 mL) and washed with 2N hydrochloric acid (500 mL) then with water (300 mL). The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was crystallized from ether/hexane to give 6.0 g of 1-(2,6-Dimethylphenyl)-3-ethyl-2-thioxo-4,5-imidazolidinedione, m.p. 103–105° C. Mass spectrum; FAB (M+H)+ m/z 263. 1H-NMR (DMSO-d6; 300 MHz): δ 7.31–7.27 (m, 1H), 7.18 (d, 2H), 3.94 (q, 2H), 2.08 (s, 6H), and 1.25 ppm (t, 3H). The mixture was heated at reflux for 1 hour then evaporated to dryness Ethanol (100 mL) was added the mixture was heated at reflux for 1 hour then evaporated to dryness The residue was dissolved in ethyl acetate (300 mL) washed with 2N hydrochloric acid (500 mL) The organic phase was dried over anhydrous magnesium sulfate evaporated to dryness The residue was crystallized from ether/hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2,6-Dimethylphenyl isothiocyanate (16.3 g; 0.1 mol) was added dropwise to 110 mL of 70% aqueous ethylamine solution. The mixture was stirred for 1 hour at ambient temperature. Excess ethylamine was evaporated under a stream of nitrogen. The mixture was diluted with water (100 mL). The solid was collected by filtration and washed with water and dried to give 20.0 g of N-(2,6-dimethylphenyl)-N′-ethylthiourea. Excess ethylamine was evaporated under a stream of nitrogen The mixture was diluted with water (100 mL) The solid was collected by filtration washed with water dried