1-(2-cyanophenyl)-3-prop-2-enylurea

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

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

Procedure: A mixture of 2-(3-allylureido)benzonitrile (10.0 g, 50 mmol) in ethanol (70 mL) and 28% of ammonia water (50 mL) was heated on a steam bath with occasional stirring for 15 minutes. The mixture was then cooled to room temperature and to the mixture was added water (100 mL). The solid was collected by filtration and was recrystallized from methanol with a few drops of ammonia water to give 8.4 g (84%) of 3,4-dihydro-4-imino-3-allyl-2(1H)-quinazolinone, mp 223°-224° C. IR (KBr): 3284, 3203, 3147, 1691, 1582 cm-1. 1H NMR (300 MHz, DMSO-d6): δ4.61 (d, 2H, =CH2), 5.08 (q, 2H, CH2), 5.85 (m, 1H, =CH), 7.07 (m, 2H, Ar--H), 7.46 (t, 1H, Ar--H), 8.04 (d, 1H, Ar--H), 8.85 (br s, 1H, NH), 10.74 (s, 1H, NH). 13C NMR (75 MHz, DMSO-d6): δ42.54, 115.08, 115.81, 122.09, 126.13, 132.77, 133.15, 137.01, 149.76. Anal. Calcd for C11H11N3O; C, 65.63; H, 5.56; N, 20.87. Found: C, 65.67; H, 5.51; N, 20.86. was heated on a steam bath The solid was collected by filtration was recrystallized from methanol with a few drops of ammonia water

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

Procedure: A mixture of anthranilonitrile (10.0 g, 85 mmol) and allyl isocyanate (7.5 mL, 85 mmol) was slightly heated to dissolve. The resulting solution was allowed to stir at room temperature for two days. The solid was collected by filtration and washed with ether (10 mL) to give 14.4 g (100%) of 2-(3-allylureido)benzonitrile. An analytical sample was recrystallized from ethanol. IR (KBr): 3331, 3263, 2226 (CN), 1639 cm-1. 1H NMR (300 MHz, DMSO-d6): δ3.74 (p, 2H, CH2), 5.09 (q, 1H, =CH), 5.17 (q, 1H, =CH), 5.86 (m, 1H, CH), 7.09 (t, 2H, Ar--H), 7.56 (t, 1H, Ar--H), 7.67 (d, 1H, Ar--H), 8.43 (d, 1H, Ar--H), 7.65 (d, 1H, NH), 8.54 (s, 1H, NH). 13C NMR (75 MHz, DMSO-d6): δ41.47, 101.00, 114.97, 116.99, 120.61, 120.73, 122.22, 132.96, 133.83, 135.69, 142.66, 154.32. Anal. Calcd for C11H11N30 (201.23): C, 65.66; H, 5.51; N, 20.89. Found: C, 65.38; H, 5.51; N, 21.05. was slightly heated to dissolve The solid was collected by filtration washed with ether (10 mL)

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

Procedure: A mixture of anthranilonitrile (10.0 g, 85 mmol) and allyl isocyanate (7.5 mL, 85 mmol) was slightly heated to dissolve. The resulting solution was allowed to stir at room temperature for two days. The solid was collected by filtration and washed with ether (10 mL) to give 14.4 g (100%) of 2-(3-allylureido)benzonitrile. An analytical sample was recrystallized from ethanol. IR (KBr): 3331, 3263, 2226 (CN), 1639 cm-1. 1H NMR (300 MHz, DMSO-d6): δ3.74 (p, 2H, CH2), 5.09 (q, 1H, =CH), 5.17 (q, 1H, =CH), 5.86 (m, 1H, CH), 7.09 (t, 2H, Ar--H), 7.56 (t, 1H, Ar--H), 7.67 (d, 1H, Ar--H), 8.43 (d, 1H, Ar--H), 7.65 (d, 1H, NH), 8.54 (s, 1H, NH). 13C NMR (75 MHz, DMSO-d6): δ41.47, 101.00, 114.97, 116.99, 120.61, 120.73, 122.22, 132.96, 133.83, 135.69, 142.66, 154.32. Anal. Calcd for C11H11N30 (201.23): C, 65.66; H, 5.51; N, 20.89. Found: C, 65.38; H, 5.51; N, 21.05. was slightly heated to dissolve The solid was collected by filtration washed with ether (10 mL)

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

Procedure: A mixture of 2-(3-allylureido)benzonitrile (10.0 g, 50 mmol) in ethanol (70 mL) and 28% of ammonia water (50 mL) was heated on a steam bath with occasional stirring for 15 minutes. The mixture was then cooled to room temperature and to the mixture was added water (100 mL). The solid was collected by filtration and was recrystallized from methanol with a few drops of ammonia water to give 8.4 g (84%) of 3,4-dihydro-4-imino-3-allyl-2(1H)-quinazolinone, mp 223°-224° C. IR (KBr): 3284, 3203, 3147, 1691, 1582 cm-1. 1H NMR (300 MHz, DMSO-d6): δ4.61 (d, 2H, =CH2), 5.08 (q, 2H, CH2), 5.85 (m, 1H, =CH), 7.07 (m, 2H, Ar--H), 7.46 (t, 1H, Ar--H), 8.04 (d, 1H, Ar--H), 8.85 (br s, 1H, NH), 10.74 (s, 1H, NH). 13C NMR (75 MHz, DMSO-d6): δ42.54, 115.08, 115.81, 122.09, 126.13, 132.77, 133.15, 137.01, 149.76. Anal. Calcd for C11H11N3O; C, 65.63; H, 5.56; N, 20.87. Found: C, 65.67; H, 5.51; N, 20.86. was heated on a steam bath The solid was collected by filtration was recrystallized from methanol with a few drops of ammonia water

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

Procedure: A mixture of anthranilonitrile (10.0 g, 85 mmol) and allyl isocyanate (7.5 mL, 85 mmol) was slightly heated to dissolve. The resulting solution was allowed to stir at room temperature for two days. The solid was collected by filtration and washed with ether (10 mL) to give 14.4 g (100%) of 2-(3-allylureido)benzonitrile. An analytical sample was recrystallized from ethanol. IR (KBr): 3331, 3263, 2226 (CN), 1639 cm-1. 1H NMR (300 MHz, DMSO-d6): δ3.74 (p, 2H, CH2), 5.09 (q, 1H, =CH), 5.17 (q, 1H, =CH), 5.86 (m, 1H, CH), 7.09 (t, 2H, Ar--H), 7.56 (t, 1H, Ar--H), 7.67 (d, 1H, Ar--H), 8.43 (d, 1H, Ar--H), 7.65 (d, 1H, NH), 8.54 (s, 1H, NH). 13C NMR (75 MHz, DMSO-d6): δ41.47, 101.00, 114.97, 116.99, 120.61, 120.73, 122.22, 132.96, 133.83, 135.69, 142.66, 154.32. Anal. Calcd for C11H11N30 (201.23): C, 65.66; H, 5.51; N, 20.89. Found: C, 65.38; H, 5.51; N, 21.05. was slightly heated to dissolve The solid was collected by filtration washed with ether (10 mL)