Dichloromethane → HCID 57265543, compound

Participants

Reaction Steps

To a solution of 2.0 g of 2,4,-difluoro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H) pyrimidinyl)benzenesulfonyl chloride and 30 ml of methylene chloride cooled to 5° C. was added 1.9 ml of a 40% solution of dimethylaminein water over 15 minutes. Analysis of the reaction mixture by TLC after 2 hours of stirring showed a single component. Work up was carried out as described in Example B-4. Two grams of crude solid was obtained and recrystallized from ethanol giving 1.7 g of a white solid, melting point 185°-194° C. NMR analysis of the product showed a 2:1 mixture of N,N-dimethyl-2,4-difluoro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)benzenesulfonamide (Compound #49) and the title compound. A mixture of 1.6 g of the product, 30 ml of methylene chloride and 3.8 ml of a 40% solution of dimethylamine in water was stirred at roomtemperature for 21 hours. The organic layer was separated, washed with water and dried over magnesium sulfate. After removal of volatiles using arotary evaporator there remained 1.6 g of a solid. Recrystallization of theproduct from ethanol gave 1.4 g of the title compound as fine white crystals, m.p. 223.5°-225° C. Spectral data for this compound is found in Table I.

Provenance & Evidence