Ammonia → HCID 71625874, compound

Participants

Reaction Steps

Following the method used to prepare 24a, the use of 50 (135 mg, 0.34 mmol) and oxalyl chloride (43 μL, 0.51 mmol) followed by reacting the intermediate acid chloride with aqueous ammonia (2 mL) provided 23 mg (17%) of product 24c as a pale yellow solid, mp 163-164° C. 1H NMR (300 MHz, CDCl3) δ 1.92-2.01 (q, J=7 Hz, 2H), 2.25 (t, J=7 Hz, 2H), 2.46 (s, 3H), 2.96 (t, J=7 Hz, 2H), 5.42 (brs, 2H), 6.84 (d, J=2 Hz, 2H), 6.96-7.00 (m, 2H), 7.21 (s, 1H), 7.38 (d, J=8 Hz, 1H), 9.34 (brs, 1H). LC-MS (CI): m/z 393.0, 395.0 [(M+H)+ C19H18Cl2N2OS requires 392.05]. Purity (100%). Calcd for C19H18Cl2N2OS: C, 58.02; H, 4.61; N, 7.12; S, 8.15; Cl, 18.03. Found: C, 58.06; H, 4.79; N, 6.88; S, 7.90; Cl, 17.75. The low yield for amide preparation in this case was due to the significant formation of a six membered lactam via cyclization of the intermediate acid chloride.

Provenance & Evidence