N-Acetylsulfanilyl chloride → HCID 178474289, compound

Participants

Reaction Steps

A stock solution of Example 14e and N,N-diisopropylethylamine (0.08 M and 0.16 M in dichloromethane, respectively, 500 μL, 0.042 mmol Example 14e and 0.083 mmol N,N-diisopropylethylamine), and 4-acetamidobenzene-1-sulfonyl chloride (0.40 M in dichloromethane, 239 μL, 0.096 mmol) were mixed and stirred at ambient temperature overnight. The reaction mixture was concentrated, dissolved in methanol (1 mL) and injected on the reverse phase HPLC(C8, acetonitrile/water (0.1% TFA), 5-100%) to yield the title compound as an impure mixture. The material was dissolved in methanol (1 mL) and manually injected into the HPLC(C8, acetonitrile/water (0.1% TFA), 5-100%) to give 0.0071 g (32%) of the title compound as the TFA salt. 1H NMR (400 MHz, DMSO-d6/D2O) δ 7.75 (q, J=9.16 Hz, 4H), 7.57 (s, 1H), 7.48 (d, J=2.44 Hz, 1H), 7.11 (d, J=8.54 Hz, 1H), 7.02 (s, 1H), 6.95 (dd, J=8.54, 2.44 Hz, 1H), 6.80 (m, J=8.85, 8.85 Hz, 2H), 6.37 (m, 2H), 4.97 (s, 1H), 4.12 (m, 1H), 4.04 (s, 3H), 2.06 (s, 3H). MS (APCI+) m/z 558.0 (M+H)+.

Provenance & Evidence