2,5-dioxopyrrole-1-carboxamide

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: A mixture of 140 g of N-carbamylmaleimide (1 mole), 130 g of 2-hydroxyethyl methacrylate (1 mole) and 1.36 g of zinc chloride (0.01 moles) in 200 mL of acetonitrile was heated to reflux. After 6 hours, the acetonitrile was evaporated and 500 mL of H2O was added. The solid was filtered and dried to afford 200 g (74% yield) of 2-hydroxyethyl methacrylate maleurate. M.P.: 62°-4° C. (dec.); 1H NMR (CDCl3): δ10.5 (br s, 1H), 8.2 (br s, 1H), 6.4 (m, 2H), 6.1 (m, 1H), 5.8 (br s, 1H), 5.6 (m, 1H), 4.4 (A2B2, 4H), 2.0 (m, 3H); 13C (CDCl3): δ167.1, 165.24, 165.23, 155.1, 135.8, 132.9, 129.6, 126.2, 63.2, 62.0, 18.2; HPLC (20% CH3CN/H2O, C18): Rt=3.5 minutes. was heated to reflux the acetonitrile was evaporated 500 mL of H2O was added The solid was filtered dried

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

実験手順: A mixture of 140 g of N-carbamylmaleimide (1 mole), 121.8 g of 2-hydroxyethyl acrylate (1.05 moles) and 1.36 g of zinc chloride (0.01 moles) in 200 mL of acetonitrile was heated to reflux. After 5 hours, the mixture was poured into 500 mL of water. The solid was filtered, washed with water and dried to afford 240.7 g (94% yield) of 2-hydroxyethyl acrylate maleurate. M.P.: 88°-90° C. (dec.); 1H NMR (CDCl3): δ10.4 (br s, 1H), 8.2 (br s, 1H), 6.4 (m, 3H), 6.2 (d of d, 1H), 5.9 (m, 2H), 4.4 (A2B2, 4H); 13C NMR (CDCl3): δ165.9, 165.3, 165.2, 155.1, 133.1, 131.6, 129.5, 127.8, 63.2, 61.9; HPLC (10% CH3CN/H2O, C18): Rt=5.7 minutes. was heated to reflux The solid was filtered washed with water dried

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

実験手順: The addition of octadecanol to N-carbamylmaleimide under the conditions of Example G afforded a 97% yield of octadecyl maleurate. M.P.: 109°-11° C. (dec.); 1H NMR (CDCl3): δ10.5 (brs, 1H), 8.2 (br s, 1H), 6.3 (m, 2H), 5.4 (br s, 1H), 4.2 (t, 2H), 1.6 (m, 2H), 1.2 (m, 30H), 0.9 (t, 3H); HPLC (80% CH3CN/H2O, C18): Rt=12.8 minutes.

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

実験手順: A mixture of 49 g of hexadecanol (0.202 moles), 28 g of N-carbamylmaleimide (0.2 moles) and 270 mg of zinc chloride (0.002 moles) in 300 mL of p-dioxane was heated to reflux. After 24 hours, the mixture was cooled to room temperature and 200 mL of H2O was added. The resulting solid was filtered, washed with additional H2O and dried to afford 75 g (97% yield) of hexadecyl maleurate. M.P.: 106°-09° C. (dec.); 1H NMR (CDCl3): δ10.5 (br s, 1H), 8.2 (br s, 1H), 6.3 (m, 2H), 5.4 (br s, 1H), 4.2 (t, 2H), 1.6 (m, 2 H), 1.2 (m, 26H), 0.9 (t, 3H); HPLC (80% CH3CN/H2O, C18): Rt=6.9 minutes. was heated to reflux The resulting solid was filtered washed with additional H2O dried

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

実験手順: The addition of 2-ethylhexanol to N-carbamylmaleimide under the conditions of Example C afforded a 95% yield of 2-ethylhexyl maleurate. M.P.: 73°-6° C.; 1H NMR (CDCl3): δ10.6 (br s, 1H), 8.2 (br s, 1H), 6.3 (m, 2H), 5.8 (br s, 1H), 4.2 (m, 2H), 1.6 (m, 1H), 1.3 (m, 8H), 0.9 (t, 6H); HPLC (40% CH3CN/H2O, C8): Rt=14.2 minutes.

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

実験手順: The addition of isopropanol to N-carbamylmaleimide under the conditions of Example C afforded a 95% yield of isopropyl maleurate. M.P.: 113°-14° C.; 1H NMR (CDCl3): δ10.6 (br s, 1H), 8.2 (br s, 1H), 6.3 (AB, 2H), 5.8 (br s, 1H), 5.2 (quintet, 1H), 1.3 (d, 6H); HPLC (20% CH3CN/H2O, C8): Rt=5.6 minutes.

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

実験手順: A mixture of 140 g of N-carbamylmaleimide (1 mole), 1.36 g of zinc chloride (0.01 moles) and 150 g of n-butanol (2 moles) was heated to reflux. After 4 hours, the mixture was poured into 400 mL of water and cooled to room temperature. The butyl maleurate was filtered, washed with water and dried to afford 200 g (93% yield). M.P.: 97°-90° C.; 1H NMR (CDCl3): δ10.6 (brs, 1H), 8.2 (brs, 1H), 6.3 (AB, 2H), 5.9 (brs, 1H), 4.2 (t, 2H), 1.6 (m, 2H), 1.4 (m, 2H), 0.9 (t, 3H); HPLC (20 to 40% CH3CN/H2O over 20 minutes, C8): Rt=9.4 minutes. was heated to reflux The butyl maleurate was filtered washed with water dried to afford 200 g (93% yield)

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

実験手順: A mixture of 5.66 g of 1,6-hexanediol (0.048 moles), 12 g of N-carbamylmaleimide (0.086 moles) and 0.3 g of zinc chloride (0.0022 moles) in 70 mL of acetonitrile was heated to reflux. After 3 hours, a lot of solid material had been produced from the mixture. The mixture was filtered and the solids washed with acetonitrile and dried to afford 12.1 9 of 1,6-hexanediol bismaleurate. was heated to reflux a lot of solid material had been produced from the mixture The mixture was filtered the solids washed with acetonitrile dried

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

実験手順: A mixture of 3 g of ethylene glycol (0.048 moles), 12 g of N-carbamylmaleimide (0.086 moles) and 0.3 g of zinc chloride (0.0022 moles) in 70 mL of acetonitrile was heated to reflux. After 3 hours, a lot of solid material had been produced from the mixture. The mixture was filtered and the solids washed with acetonitrile and dried to afford 11.7 g of ethylene glycol bismaleurate. M.P.: 158°-60° C.; 1H NMR (DMSO-d6): δ 10.5 (s, 2 H), 7.2-7.8 (m, 4 H), 6.2-6.4 (m,4H),4.3(s,4H). was heated to reflux a lot of solid material had been produced from the mixture The mixture was filtered the solids washed with acetonitrile dried

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

実験手順: A mixture of 9.86 g of trimethylolpropane (0.074 moles), 31.3 g of N-carbamylmaleimide (0.224 moles) and 0.85 g of zinc chloride (0.00625 moles) in 215 mL of acetonitrile was heated to reflux. After 5 hours, the acetonitrile was evaporated to afford 40.7 g of trimethylolpropane trimaleurate as a white solid. M.P.: 70°-76° C.; 1H NMR (DMSO-d6): δ 10.5 (s, 3 H), 7.2-7.7 (m, 6 H), 6.3-6.6 (m, 6 H), 4.1 (s, 6 H), 1.35 (q, 2 H), 1.85 (t, 3 H). was heated to reflux the acetonitrile was evaporated

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

実験手順: A mixture of 5.66 g of 1,6-hexanediol (0.048 moles), 12 g of N-carbamylmaleimide (0.086 moles) and 0.3 g of zinc chloride (0.0022 moles) in 70 mL of acetonitrile was heated to reflux. After 3 hours, a lot of solid material had been produced from the mixture. The mixture was filtered and the solids washed with acetonitrile and dried to afford 12.1 g of 1,6-hexanediol bismaleurate. was heated to reflux a lot of solid material had been produced from the mixture The mixture was filtered the solids washed with acetonitrile dried