HCID 11046378, compound → HCID 10970290, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(5-amino-4-chloro-2-nitro-phenylthio)-N,N-dimethyl-benzamide (18) (1 g, 2.84 mmol) in 6 N HCl (10 mL), a solution of sodium nitrite (0.3 g, 4.35 mmol) in wter (0.5 mL) was added at −5° C. (−0° C.). To this mixture, 48% hexafluorophosphoric acid (1.5 mL) was added at 0° C. and the mixture was stirred for 10 min. The precipitate was collected by filtration. The deep red solid was washed with ice water and air-dried using suction filter. The solid was further dried under high vacuum for several hours. The red powder was heated at 170° C. using oil bath until gas evolution was no longer observed. Dark colored residue was purified by silica gel chromatography to yield 380 mg of (19) (37%). IR (cm−1, neat) 2927, 1634, 1521, 1465, 1400, 1336, 1282, 1249, 1091, 1H NMR (200 MHz CDCl3) δ 8.32 (d, J=2.8 Hz, 1H), 7.4–7.6 (m, 4H), 6.67 (d, J=5.0 Hz, 1H), 3.04 (s, 3H), 2.84 (s, 3H). Anal. (C15H12ClFN2O3S) C, H, N.

Provenance & Evidence