4-amino-N-methyl-N-phenylbenzenesulfonamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of N-(4-chlorosulfonylphenyl)phosphoramidic dichloride (1.0 g) and N-methylaniline (2.49 g) in water (5 ml) was heated at reflux for 18 hours. After cooling to 0° C. and adjustment to pH2 with concentrated hydrochloric acid, the suspension was heated at reflux for 30 minutes, then cooled to 0° C. and adjusted to pH 8 with concentrated ammonium hydroxide. The suspension was extracted with ethyl acetate (3×40 ml), the combined organic extracts were washed with brine, dried (Na2SO4), and concentrated to an oil. Purification by chromatography (3:2 hexane: ethyl acetate) gave 4-(N-phenyl-N-methylaminosulfonyl)aniline as a colourless crystalline solid (0.65 g); MS: m/z=263(M+1); NMR (CDCl3): 3.13 (s,3), 4.11 (broad s,2), 6.58-6.62 (m, 2), 7.10-7.13 (m,2), 7.23-7.31 (m,s). was heated at reflux for 18 hours at reflux for 30 minutes cooled to 0° C. The suspension was extracted with ethyl acetate (3×40 ml) the combined organic extracts were washed with brine dried (Na2SO4) concentrated to an oil Purification by chromatography (3:2 hexane: ethyl acetate)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cooled (-20° C.) solution of α-trifluoromethyl lactic acid 0.20 g in dry N,N-dimethylacetamide (4 ml) was added thionyl chloride (0.16 g). The reaction mixture was stirred for 1 hour, then warmed to 0° C. over 30 minutes and treated with 4-(N-phenyl-N-methylaminosulfonyl)aniline (0.34 g). After stirring at 22° C. for 24 hours, the reaction mixture was diluted with water (30 ml) and extracted with ethyl acetate (2×20 ml). The combined ethyl acetate extracts were washed with brine, dried (Na2SO4) and concentrated at reduced pressure to give an oil which was purified by chromatography (1:1 hexane: ethyl aceate) and recrystallised from methyl-t-butyl ether/hexane to produce the title compound as a colourless solid (0.31 g); mp 147°-149° C.; MS: m/z=403(M+1); NMR (250 MHz): 1.55 (s,3), 3.09 (s,3), 7.05-7.08 (m, 2), 7.28-7.43 (m,5), 7.53 (s,1), 7.91-7.95 (m,2), 10.36 (broad s, 1). Analysis for C17H17F3N2O4S: Calculated: C, 50.78; H, 4.26; N, 6.97; Found: C, 50.80; H, 4.37; N, 6.93. After stirring at 22° C. for 24 hours extracted with ethyl acetate (2×20 ml) The combined ethyl acetate extracts were washed with brine dried (Na2SO4) concentrated at reduced pressure to give an oil which was purified by chromatography (1:1 hexane: ethyl aceate) recrystallised from methyl-t-butyl ether/hexane