2,5-dichloro-N-(oxomethylidene)benzenesulfonamide

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

Procedure: To a stirred mixture of 0.8 g of 2-methylamino-4-methoxy-6-methylpyrimidine in 25 ml of acetonitrile containing a few crystals of 1,4-diazabicyclo[2.2.2]octane was added dropwise 1.3 g of 2,5-dichlorobenzenesulfonyl isocyanate. The mixture was stirred for 16 hours and the resultant solid was filtered to afford 1.2 g of N-[N-(4-methoxy-6-methylpyrimidine-2-yl)-N-methylaminocarbonyl]-2,5-dichlorobenzenesulfonamide melting at 182°-185°. Infrared absorption spectrum showed peaks at 1690 cm-1, 1590 cm-1, and 1550 cm-1 which are typical for this type of compound. the resultant solid was filtered

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

Procedure: A solution of one gram (0.0031 mole) 2-[4-(4-trifluoromethylphenoxy)phenoxy]-propionic acid in dry CHCH3 was treated with 0.8 gram (g) (0.0081 mole) 2,5-dichlorobenzene sulfonyl isocyanate. The solution was stirred for approximately 18 hours, then heated to reflux for three hours, followed by cooling. heated to reflux for three hours by cooling

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

Procedure: A solution of one gram (0.0031 mole) 2-[4-(4-trifluoromethylphenoxy)phenoxy]-propionic acid in dry CHCH3 was treated with 0.8 gram (g) (0.0081 mole) 2,5-dichlorobenzene sulfonyl isocyanate. The solution was stirred for approximately 18 hours, then heated to reflux for three hours, followed by cooling. heated to reflux for three hours by cooling

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

Procedure: To a stirred mixture of 0.8 g of 2-methylamino-4-methoxy-6-methylpyrimidine in 25 ml of acetonitrile containing a few crystals of 1,4-diazabicyclo[2.2.2]octane was added dropwise 1.3 g of 2,5-dichlorobenzenesulfonyl isocyanate. The mixture was stirred for 16 hours and the resultant solid was filtered to afford 1.2 g of N-[N-(4-methoxy-6-methylpyrimidine-2-yl)-N-methylaminocarbonyl]-2,5-dichlorobenzenesulfonamide melting at 182°-185°. Infrared absorption spectrum showed peaks at 1690 cm-1, 1590 cm-1, and 1550 cm-1 which are typical for this type of compound. the resultant solid was filtered

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

Procedure: To a stirred mixture of 0.8 g of 2-methylamino-4-methoxy-6-methylpyrimidine in 25 ml of acetonitrile containing a few crystals of 1,4-diazabicyclo[2.2.2]octane was added dropwise 1.3 g of 2,5-dichlorobenzenesulfonyl isocyanate. The mixture was stirred for 16 hours and the resultant solid was filtered to afford 1.2 g of N-[N-(4-methoxy-6-methylpyrimidine-2-yl)-N-methylaminocarbonyl]-2,5-dichlorobenzenesulfonamide melting at 182°-185°. Infrared absorption spectrum showed peaks at 1690 cm-1, 1590 cm-1, and 1550 cm-1 which are typical for this type of compound. the resultant solid was filtered

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

Procedure: To a stirred mixture of 0.8 g of 2-methylamino-4-methoxy-6-methylpyrimidine in 25 ml of acetonitrile containing a few crystals of 1,4-diazabicyclo[2.2.2]octane was added dropwise 1.3 g of 2,5-dichlorobenzenesulfonyl isocyanate. The mixture was stirred for 16 hours and the resultant solid was filtered to afford 1.2 g of N-[N-(4-methoxy-6-methylpyrimidine-2-yl)-N-methylaminocarbonyl]-2,5-dichlorobenzenesulfonamide melting at 182°-185°. Infrared absorption spectrum showed peaks at 1690 cm-1, 1590 cm-1, and 1550 cm-1 which are typical for this type of compound. the resultant solid was filtered

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

Procedure: To a stirred mixture of 0.8 g of 2-methylamino-4-methoxy-6-methylpyrimidine in 25 ml of acetonitrile containing a few crystals of 1,4-diazabicyclo[2.2.2]octane was added dropwise 1.3 g of 2,5-dichlorobenzenesulfonyl isocyanate. The mixture was stirred for 16 hours and the resultant solid was filtered to afford 1.2 g of N-[N-(4-methoxy-6-methylpyrimidine-2-yl)-N-methylaminocarbonyl]-2,5-dichlorobenzenesulfonamide melting at 182°-185°. Infrared absorption spectrum showed peaks at 1690 cm-1, 1590 cm-1, and 1550 cm-1 which are typical for this type of compound. the resultant solid was filtered

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

Procedure: 1.12 g (4.42 mmol) of 2,5-dichlorobenzenesulfonylisocyanate and 882 mg (4.42 mmol) of 2-amino-4-chlorobenzoic acid were treated in the same way as in Example 1 to obtain 1.06 g of the above-identified compound (yield 58.6%). Properties: colorless crystal, Melting point: 254°-256° C., PMR (δppm, DMSO-d6):7.17 (1H,s), 7.24 (1H,d), 7.71 (1H,d), 7.80-7.89 (2H,m), 8.18 (1H,s).

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

Procedure: To a stirred mixture of 0.8 g of 2-methylamino-4-methoxy-6-methylpyrimidine in 25 ml of acetonitrile containing a few crystals of 1,4-diazabicyclo[2.2.2]octane was added dropwise 1.3 g of 2,5-dichlorobenzenesulfonyl isocyanate. The mixture was stirred for 16 hours and the resultant solid was filtered to afford 1.2 g of N-[N-(4-methoxy-6-methylpyrimidine-2-yl)-N-methylaminocarbonyl]-2,5-dichlorobenzenesulfonamide melting at 182°-185°. Infrared absorption spectrum showed peaks at 1690 cm-1, 1590 cm-1, and 1550 cm-1 which are typical for this type of compound. the resultant solid was filtered

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

Procedure: A suspension of 452 g of 2,5-dichlorobenzene sulfonamide, 260 g of cyclohexylisocyanate and 10.0 g of "Dabco" (1,4-diazabicyclo[2,2,2]octane) in 2000 ml chlorobenzene was heated for one hour to reflux in a flask fitted with a water condenser and dry-ice condenser in series, a stirrer and a thermometer. Phosgene was then added into the vapor space of the flask at such a rate that the temperature of the reaction mass was maintained at 123°-125° C. due to refluxing phosgene. During 3 hours of operation a total of 260 g of phosgene was added. The dry-ice condenser was then removed and the reaction mass refluxed to drive off excess phosgene until the temperature reached 134° C. After cooling to room temperature and filtration, the solvent and cyclohexylisocyanate were recovered by distillation at 100 mm pressure. The resulting residue was then distilled at lower pressure. Obtained were 378 g (75% yield) of 2,5-dichlorobenzenesulfonylisocyanate (B.P. 105° C./0.35 mm). was heated for one hour to reflux in a flask fitted with a water condenser and dry-ice condenser in series, a stirrer was maintained at 123°-125° C. due The dry-ice condenser was then removed the reaction mass refluxed reached 134° C filtration the solvent and cyclohexylisocyanate were recovered by distillation at 100 mm pressure The resulting residue was then distilled at lower pressure Obtained

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

Procedure: A solution of one gram (0.0031 mole) 2-[4-(4-trifluoromethylphenoxy)phenoxy]-propionic acid in dry CHCH3 was treated with 0.8 gram (g) (0.0081 mole) 2,5-dichlorobenzene sulfonyl isocyanate. The solution was stirred for approximately 18 hours, then heated to reflux for three hours, followed by cooling. heated to reflux for three hours by cooling

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

Procedure: To a stirred mixture of 0.8 g of 2-methylamino-4-methoxy-6-methylpyrimidine in 25 ml of acetonitrile containing a few crystals of 1,4-diazabicyclo[2.2.2]octane was added dropwise 1.3 g of 2,5-dichlorobenzenesulfonyl isocyanate. The mixture was stirred for 16 hours and the resultant solid was filtered to afford 1.2 g of N-[N-(4-methoxy-6-methylpyrimidine-2-yl)-N-methylaminocarbonyl]-2,5-dichlorobenzenesulfonamide melting at 182°-185°. Infrared absorption spectrum showed peaks at 1690 cm-1, 1590 cm-1, and 1550 cm-1 which are typical for this type of compound. the resultant solid was filtered