1-bromo-3-isocyanatobenzene

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:

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

Procedure: 3-Bromophenyl isocyanate (21.12 g, 107 mmol) was added slowly to a stirred solution of 2,2,2-trifluoroethyl amine (40 ml, 0.5 mol) in THF (100 mL) at 0° C. under N2, rinsing with THF (25 mL). The reaction was allowed to warm slowly to RT and kept at this temperature for 16 hours. The volatiles were removed under reduced pressure to give the title compound (31.6 g) as a solid. 1H NMR (400 MHz, DMSO-d6) δ 8.94 (1H, s), 7.80 (1H, t), 7.31-7.24 (1H, m), 7.20 (1H, t), 7.16-7.08 (1H, m), 6.83 (1H, bt), 3.98-3.85 (2H, m). rinsing with THF (25 mL) The volatiles were removed under reduced pressure

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

Procedure: 3-Bromophenyl isocyanate (21.12 g, 107 mmol) was added slowly to a stirred solution of 2,2,2-trifluoroethyl amine (40 ml, 0.5 mol) in THF (100 mL) at 0° C. under N2, rinsing with THF (25 mL). The reaction was allowed to warm slowly to RT and kept at this temperature for 16 hours. The volatiles were removed under reduced pressure to give the title compound (31.6 g) as a solid. 1H NMR (400 MHz, DMSO-d6) δ 8.94 (1H, s), 7.80 (1H, t), 7.31-7.24 (1H, m), 7.20 (1H, t), 7.16-7.08 (1H, m), 6.83 (1H, bt), 3.98-3.85 (2H, m). rinsing with THF (25 mL) The volatiles were removed under reduced pressure

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

Procedure: N-(2-Hydroxy-4-nitrophenyl)-N′-(3-bromo phenyl)urea was prepared from 2-hydroxy 4-nitro aniline (500 mg, 3.24 mmol) and 3-bromo phenyl isocyanate (3.24 mmol) according to the procedure in General Method B. The product was purified by dilution with methylene chloride and precipitation with hexanes. Filtering afforded the title compound (0.96 g, 87%). EI-MS m/z 350 (M−H)− The product was purified by dilution with methylene chloride and precipitation with hexanes Filtering

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

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

Procedure: 3-Bromophenyl isocyanate (1.0 ml, 8.1 mmol) was added slowly to a stirred solution of 2,2,2-trifluoroethyl amine (3.2 ml, 40 mmol) in THF (10 ml) at 0° C. under N2. After 1 hour the reaction was allowed to warm to RT and kept at this temperature for 16 hours. The volatiles were removed in vacuo to give the title compound (2.5 g, solid). 1H NMR (400 MHz, DMSO-d6): 9.00 (1H, s), 7.86 (1H, t), 7.33 (1H, ddd), 7.26 (1H, t), 7.18 (1H, ddd), 6.89 (1H, t), 4.03-3.92 (2H, m). kept at this temperature for 16 hours The volatiles were removed in vacuo

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

Procedure: Equimolar amounts of 3(R)-amino-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one and 3-bromophenylisocyanate were mixed in 8 ml of dry tetrahydrofuran at room temperature. The reaction mixture was allowed to stand for 8 hours and was then filtered. The collected solids were washed with tetrahydrofuran and dried in vacuo over P2O5 to give the analytical product: m.p. 194°-196° C. was then filtered The collected solids were washed with tetrahydrofuran dried in vacuo over P2O5 to give the analytical product

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

Procedure: 4-Amino-5-(4-methoxyphenoxy)quinazoline (0.35 g, 1.3 mmol) and 3-bromophenyl isocyanate (0.31 g, 1.6 mmol) were reacted in 20 ml of dichloromethane according to procedure E to give 1-[5-(4-methoxyphenoxy)quinazolin-4-yl]-3-(3-bromophenyl)urea (0.5 g, 83.3%, m.p. 249-251° C.)

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

Procedure: 4-Amino-5-(4-methoxyphenoxy)quinazoline (0.35 g, 1.3 mmol) and 3-bromophenyl isocyanate (0.31 g, 1.6 mmol) were reacted in 20 ml of dichloromethane according to procedure E to give 1-[5-(4-methoxyphenoxy)quinazolin-4-yl]-3-(3-bromophenyl)urea (0.5 g, 83.3%, m.p. 249-251° C.)