methyl 2-isocyanatobenzoate

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:

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: A solution of 2-methoxycarbonylphenyl isocyanate (1.0 g, 5.6 mmol), N-methyl-2-iodoaniline, hydrochloride (1.6 g, 5.9 mmol) and N,N-diisopropylethylamine (1.1 mL, 6.3 mmol) in 100 mL of toluene was refluxed under N2 for 72 hours. The sample was concentrated, and partitioned between chloroform and 10% HCl. The chloroform was dried (MgSO4), filtered, concentrated and chromatographed (silica gel, methylene chloride) to give the title compound as a yellow solid, mp 144°-148° C. The sample was concentrated partitioned between chloroform and 10% HCl The chloroform was dried (MgSO4) filtered concentrated chromatographed (silica gel, methylene chloride)

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

Procedure: A solution of 2-methoxycarbonylphenyl isocyanate (1.0 g, 5.6 mmol), N-methyl-2-iodoaniline, hydrochloride (1.6 g, 5.9 mmol) and N,N-diisopropylethylamine (1.1 mL, 6.3 mmol) in 100 mL of toluene was refluxed under N2 for 72 hours. The sample was concentrated, and partitioned between chloroform and 10% HCl. The chloroform was dried (MgSO4), filtered, concentrated and chromatographed (silica gel, methylene chloride) to give the title compound as a yellow solid, mp 144°-148° C. The sample was concentrated partitioned between chloroform and 10% HCl The chloroform was dried (MgSO4) filtered concentrated chromatographed (silica gel, methylene chloride)

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

Procedure: A solution of 2-methoxycarbonyl phenylisocyanate (21.7 g) in ethyl acetate (116 g) is added dropwise to N-methylethanolamine (22.5 g), the mixture being stirred and cooled to keep the temperature below 36° C. The upper layer of the resulting mixture is separated and distilled at 60° C. under reduced pressure to remove ethyl acetate. The white solid residue remaining is triturated with ether, filtered, washed with ether and then dried in air to give N-(2-methoxycarbonylphenyl)-N'-methyl-N'-(2-hydroxyethyl)urea (22.4 g), m.pt. 90° C. cooled the temperature below 36° C The upper layer of the resulting mixture is separated distilled at 60° C. under reduced pressure to remove ethyl acetate The white solid residue remaining is triturated with ether filtered washed with ether dried in air

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

Procedure: To a solution of methyl 2-isocyanatobenzoate (0.97 g, 5.5 mmol) and Boc 1,4-phenylenediamine (1.04 g, 5 mmol) in THF (15 mL) was added DIEA (0.87 mL, 5 mmol) and DBU (0.75 mL, 5 mmol). The reaction mixture stirred at room temp for 5 hr, the off-white solid filtered and washed with ethyl ether to give desired compound (1.49 g, 85%). ES-MS (M+Na)+=376.1, (M−tBu+H)+=298.0. the off-white solid filtered washed with ethyl ether

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

Procedure: To a solution of methyl 2-isocyanatobenzoate (0.97 g, 5.5 mmol) and Boc 1,4-phenylenediamine (1.04 g, 5 mmol) in THF (15 mL) was added DIEA (0.87 mL, 5 mmol) and DBU (0.75 mL, 5 mmol). The reaction mixture stirred at room temp for 5 hr, the off-white solid filtered and washed with ethyl ether to give desired compound (1.49 g, 85%). ES-MS (M+Na)+=376.1, (M−tBu+H)+=298.0. the off-white solid filtered washed with ethyl ether