1-benzyl-2-isocyanatobenzene

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of anhydrous aluminum chloride (319 mg, 2.39 mmol) in o-xylene is heated to 110° C. Then, a solution of 2-benzylphenylisocyanate (500 mg, 2.39 mmol) is added dropwise and the brown reaction mixture is kept stirring at 150° C. during 1 h. After cooling to rt, the solvent is evaporated, the residue is dissolved in dichloromethane/methanol (19:1) and filtered through a small plug of silica gel. The solvent is evaporated and the crude product is recrystallized from acetonitrile to give pure subtitle compound as a beige solid (170 mg) in 34% yield (Warawa et al., J. Med. Chem. 2001, 44, 372-389): tR (LC-2) 1.87 min; ESI-MS(+): m/z 210.13 [M+H]+ (calcd 209.24 for C14H11NO). After cooling to rt the solvent is evaporated the residue is dissolved in dichloromethane/methanol (19:1) filtered through a small plug of silica gel The solvent is evaporated the crude product is recrystallized from acetonitrile

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

Procedure: Reagents: Benzylisothiocyanate (6.5 mmol, 0.85 mL), 2-benzylphenyl-isocyanate (6.5 mmol, 0.82 mL) and SO2Cl2 (6.5 mmol, 0.5 mL) in diethyl ether (25 mL). Isolation: filtration of reaction mixture. Purification: recrystallization from EtOH Isolation: filtration of reaction mixture Purification recrystallization from EtOH

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

Procedure: Reagents: Benzylisothiocyanate (6.5 mmol, 0.85 mL), 2-benzylphenyl-isocyanate (6.5 mmol, 0.82 mL) and SO2Cl2 (6.5 mmol, 0.5 mL) in diethyl ether (25 mL). Isolation: filtration of reaction mixture. Purification: recrystallization from EtOH Isolation: filtration of reaction mixture Purification recrystallization from EtOH

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

Procedure: Reagents: Benzylisothiocyanate (6.5 mmol, 0.85 mL), 2-benzylphenyl-isocyanate (6.5 mmol, 0.82 mL) and SO2Cl2 (6.5 mmol, 0.5 mL) in diethyl ether (25 mL). Isolation: filtration of reaction mixture. Purification: recrystallization from EtOH Isolation: filtration of reaction mixture Purification recrystallization from EtOH

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of anhydrous aluminum chloride (319 mg, 2.39 mmol) in o-xylene is heated to 110° C. Then, a solution of 2-benzylphenylisocyanate (500 mg, 2.39 mmol) is added dropwise and the brown reaction mixture is kept stirring at 150° C. during 1 h. After cooling to rt, the solvent is evaporated, the residue is dissolved in dichloromethane/methanol (19:1) and filtered through a small plug of silica gel. The solvent is evaporated and the crude product is recrystallized from acetonitrile to give pure subtitle compound as a beige solid (170 mg) in 34% yield (Warawa et al., J. Med. Chem. 2001, 44, 372-389): tR (LC-2) 1.87 min; ESI-MS(+): m/z 210.13 [M+H]+ (calcd 209.24 for C14H11NO). After cooling to rt the solvent is evaporated the residue is dissolved in dichloromethane/methanol (19:1) filtered through a small plug of silica gel The solvent is evaporated the crude product is recrystallized from acetonitrile

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

Procedure: Reagents: Benzylisothiocyanate (6.5 mmol, 0.85 mL), 2-benzylphenyl-isocyanate (6.5 mmol, 0.82 mL) and SO2Cl2 (6.5 mmol, 0.5 mL) in diethyl ether (25 mL). Isolation: filtration of reaction mixture. Purification: recrystallization from EtOH Isolation: filtration of reaction mixture Purification recrystallization from EtOH