isocyanato(methylsulfonyl)methane

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

Procedure: Isocyanato(methylsulfonyl)methane (440 mg, 3.25 mmol) was added dropwise in the dark under nitrogen to a stirred suspension of E)-4-(2-(4-diazo-4H-imidazol-5-yl)vinyl)benzonitrile (600 mg, 2.71 mmol) in DMSO (6 mL) and the mixture was stirred overnight. The resulting solution was poured into ice and the precipitate was filtered and washed successively with water, ethyl acetate and diethyl ether. The crude product was dried under vacuum and was absorbed on silica and purified by flash chromatography using DCM:MeCN (90:10) as eluent to give the pure title compound as a bright yellow solid (31 mg, 3% yield). δH (DMSO d6): 8.95 (1H, s), 7.95-7.97 (2H, d, J=8.6), 7.84-7.87 (2H, d, J=8.6), 7.75 (2H, s), 5.76 (2H, s), 3.16 (3H, s). The resulting solution was poured into ice the precipitate was filtered washed successively with water, ethyl acetate and diethyl ether The crude product was dried under vacuum was absorbed on silica purified by flash chromatography

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

Procedure: Isocyanato-methanesulfonyl-methane (250 mg, 1.85 mmol) was added drop wise to a suspension of 5-diazoimidazole-4-carboxamide (210 mg, 1.53 mmol) in dry DMSO (2 mL) at room temperature under nitrogen. The resulting mixture was stirred at room temperature for 72 hours. The reaction was quenched by the pouring onto crushed ice. The resultant precipitate was collected by filtration and washed with Et2O (3 reaction volumes) and dried to give the title compound as a white solid (283 mg, 68%). 1H NMR (400 MHz, d6-DMSO) δ ppm: 8.94 (1H, s), 7.90 (1H, s), 7.75 (1H, s), 5.82 (2H, s), 3.15 (3H, s). The reaction was quenched by the pouring onto crushed ice The resultant precipitate was collected by filtration washed with Et2O (3 reaction volumes) dried

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

Procedure: Isocyanato(methylsulfonyl)methane (440 mg, 3.25 mmol) was added dropwise in the dark under nitrogen to a stirred suspension of E)-4-(2-(4-diazo-4H-imidazol-5-yl)vinyl)benzonitrile (600 mg, 2.71 mmol) in DMSO (6 mL) and the mixture was stirred overnight. The resulting solution was poured into ice and the precipitate was filtered and washed successively with water, ethyl acetate and diethyl ether. The crude product was dried under vacuum and was absorbed on silica and purified by flash chromatography using DCM:MeCN (90:10) as eluent to give the pure title compound as a bright yellow solid (31 mg, 3% yield). δH (DMSO d6): 8.95 (1H, s), 7.95-7.97 (2H, d, J=8.6), 7.84-7.87 (2H, d, J=8.6), 7.75 (2H, s), 5.76 (2H, s), 3.16 (3H, s). The resulting solution was poured into ice the precipitate was filtered washed successively with water, ethyl acetate and diethyl ether The crude product was dried under vacuum was absorbed on silica purified by flash chromatography