4-isocyanatobutylbenzene

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

Procedure: Following the synthetic procedure of 4b′ as described in Example 17, isocyanate 4c′ (84% yield) was synthesized from 4-(phenyl)butylamine as an oil. 1H-NMR (CDCl3) δ1.61-1.78 (m, 4H), 2.66 (t, J=7.5 Hz, 2H), 3.32 (t, J=6.5 Hz, 2H), 7.17-7.23 (m, 3H), 7.26-7.32 (m, 2H).

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

Procedure: Following the synthetic procedure of 4b′ as described in Example 17, isocyanate 4c′ (84% yield) was synthesized from 4-(phenyl)butylamine as an oil. 1H-NMR (CDCl3) δ1.61-1.78 (m, 4H), 2.66 (t, J=7.5 Hz, 2H), 3.32 (t, J=6.5 Hz, 2H), 7.17-7.23 (m, 3H), 7.26-7.32 (m, 2H).

Conditions: temp:22.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (4-Isocyanatobutyl)benzene (463 mg, 2.64 mmol) was added dropwise to a stirred solution of 1H-benzo[d][1,2,3]triazole (300 mg, 2.52 mmol) in DCM (18 ml) at 0-5° C. The clear reaction mixture was allowed to stir at 20-25° C. overnight. The solvent was removed in vacuum to give a clear oil. The oil solidified on standing into a colourless solid. The product was recrystallised from 2-propanol, the solid was collected, dried in vacuum at 45° C. Yield 477 mg (64%). The solvent was removed in vacuum to give a clear oil The product was recrystallised from 2-propanol the solid was collected dried in vacuum at 45° C

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

Procedure: Uracil (0.10 g, 0.89 mmol) was dissolved in dry pyridine (4.4 mL). DMAP (0.12 g, 0.96 mmol) was added and the reaction mixture was stirred under nitrogen atmosphere at room temperature for 30 min. 4-Phenyl butyl isocyanate (0.27 mL, 1.60 mmol, 1.8 equiv) was then added and the resulting mixture was stirred for 12 hrs. The solvent was evaporated under reduced pressure and the crude was purified by column chromatography using a Teledyne ISCO apparatus (cyclohexane:EtOAc from 50:50 to 30:70) to afford the title compound (0.10 g, 59%) as white powder. 1H NMR (400 MHz, CDCl3): δ 1.59-1.82 (m, 4H), 2.66 (t, J=7.2 Hz, 2H), 3.29-3.60 (m, 2H), 5.89 (d, J=8.5 Hz, 1H), 7.11-7.22 (m, 3H), 723-734 (m, 2H), 8.41 (d, J=8, 5 Hz, 1H), 8.66 (s, 1H), 9.06 (t, J=5.7 Hz, 1H). 13C NMR (101 MHz, CDCl3): δ 28.69, 28.92, 35.56, 41.23, 77.16, 104.01, 126.06, 128.53, 139.08, 141.95, 149.84, 151.51, 162.30 MS (ESI) m/z: 310 [M-N]−. the resulting mixture was stirred for 12 hrs The solvent was evaporated under reduced pressure the crude was purified by column chromatography

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

Procedure: Following the synthetic procedure of 4b′ as described in Example 17, isocyanate 4c′ (84% yield) was synthesized from 4-(phenyl)butylamine as an oil. 1H-NMR (CDCl3) δ1.61-1.78 (m, 4H), 2.66 (t, J=7.5 Hz, 2H), 3.32 (t, J=6.5 Hz, 2H), 7.17-7.23 (m, 3H), 7.26-7.32 (m, 2H).

Conditions: temp:22.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (4-Isocyanatobutyl)benzene (463 mg, 2.64 mmol) was added dropwise to a stirred solution of 1H-benzo[d][1,2,3]triazole (300 mg, 2.52 mmol) in DCM (18 ml) at 0-5° C. The clear reaction mixture was allowed to stir at 20-25° C. overnight. The solvent was removed in vacuum to give a clear oil. The oil solidified on standing into a colourless solid. The product was recrystallised from 2-propanol, the solid was collected, dried in vacuum at 45° C. Yield 477 mg (64%). The solvent was removed in vacuum to give a clear oil The product was recrystallised from 2-propanol the solid was collected dried in vacuum at 45° C