1-chloro-N-methylmethanesulfonamide

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

Procedure: A 50-ml flask was charged with 5.0 grams (0.035 mol) of N-methyl chloromethane sulfonyl chloride (from Example 1) and 5.3 grams (0.035 mol) of p-chlorophenylisocyanate. Then 3 ml of triethylamine were added. There was an exothermic reaction, and the mixture turned solid. After standing for 3/4 hour at 25° C., ether was added to form a slurry. This slurry was filtered to give a white solid which was reslurried in ether, filtered and dried to give 2.7 grams of 4-p-chlorophenyl-1,2,4-thiadiazolidine-1,1,3-trione having a melting point of 155°-157° C. Analysis for C9H9ClN2O3S: S, 12.3%; Cl, 13.6%. Found, S, 12.4%; Cl, 13.7%. The infrared spectra had strong absorption at 1720, 1485, 1435, 1370, 1340, 1280, 1255, and 1145 cm-1. The NMR spectra in 6D-dimethylsulfoxide had major peaks at 7.7 (4H), 5.6 (2H), and 3.3 (3H) ppm, and minor peaks at 4.0 and 2.8 ppm. an exothermic reaction After standing for 3/4 hour at 25° C. to form a slurry This slurry was filtered to give a white solid which filtered dried

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 19 g of 3,4-dichlorophenyl isocyanate in 150 ml of ethyl ether was added to a solution of 14.4 g of N-methyl-N-chloromethylsulfonyl-amine in 150 ml of ethyl ether and after the addition of 0.1 ml of triethylamine, the mixture was stirred for a hour at 20° C. The crystals formed were recovered by vacuum filtration, were washed, dried and dissolved in chloroform. The insolubles were removed by filtration and the filtrate was concentrated to dryness. The product was crystallized from methyl ethyl ketone to obtain 21.3 g of N-methyl-N-chloromethylsulfonyl-N'-(3,4-dichlorophenyl)-urea melting at 119° C. The crystals formed were recovered by vacuum filtration were washed dried dissolved in chloroform The insolubles were removed by filtration the filtrate was concentrated to dryness The product was crystallized from methyl ethyl ketone

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 19 g of 3,4-dichlorophenyl isocyanate in 150 ml of ethyl ether was added to a solution of 14.4 g of N-methyl-N-chloromethylsulfonyl-amine in 150 ml of ethyl ether and after the addition of 0.1 ml of triethylamine, the mixture was stirred for a hour at 20° C. The crystals formed were recovered by vacuum filtration, were washed, dried and dissolved in chloroform. The insolubles were removed by filtration and the filtrate was concentrated to dryness. The product was crystallized from methyl ethyl ketone to obtain 21.3 g of N-methyl-N-chloromethylsulfonyl-N'-(3,4-dichlorophenyl)-urea melting at 119° C. The crystals formed were recovered by vacuum filtration were washed dried dissolved in chloroform The insolubles were removed by filtration the filtrate was concentrated to dryness The product was crystallized from methyl ethyl ketone

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

Procedure: A 50-ml flask was charged with 5.0 grams (0.035 mol) of N-methyl chloromethane sulfonyl chloride (from Example 1) and 5.3 grams (0.035 mol) of p-chlorophenylisocyanate. Then 3 ml of triethylamine were added. There was an exothermic reaction, and the mixture turned solid. After standing for 3/4 hour at 25° C., ether was added to form a slurry. This slurry was filtered to give a white solid which was reslurried in ether, filtered and dried to give 2.7 grams of 4-p-chlorophenyl-1,2,4-thiadiazolidine-1,1,3-trione having a melting point of 155°-157° C. Analysis for C9H9ClN2O3S: S, 12.3%; Cl, 13.6%. Found, S, 12.4%; Cl, 13.7%. The infrared spectra had strong absorption at 1720, 1485, 1435, 1370, 1340, 1280, 1255, and 1145 cm-1. The NMR spectra in 6D-dimethylsulfoxide had major peaks at 7.7 (4H), 5.6 (2H), and 3.3 (3H) ppm, and minor peaks at 4.0 and 2.8 ppm. an exothermic reaction After standing for 3/4 hour at 25° C. to form a slurry This slurry was filtered to give a white solid which filtered dried

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 19 g of 3,4-dichlorophenyl isocyanate in 150 ml of ethyl ether was added to a solution of 14.4 g of N-methyl-N-chloromethylsulfonyl-amine in 150 ml of ethyl ether and after the addition of 0.1 ml of triethylamine, the mixture was stirred for a hour at 20° C. The crystals formed were recovered by vacuum filtration, were washed, dried and dissolved in chloroform. The insolubles were removed by filtration and the filtrate was concentrated to dryness. The product was crystallized from methyl ethyl ketone to obtain 21.3 g of N-methyl-N-chloromethylsulfonyl-N'-(3,4-dichlorophenyl)-urea melting at 119° C. The crystals formed were recovered by vacuum filtration were washed dried dissolved in chloroform The insolubles were removed by filtration the filtrate was concentrated to dryness The product was crystallized from methyl ethyl ketone