AKOS BC-3092 synthesis

Yield:39542-27-3 78%

Reaction Conditions:

in chloroform at 0 - 20; for 1.333 h;

Steps:

Synthesis of chloromethylsulfonamides 2d,e (general procedure).

General procedure: A solution of amine (40 mmol) in CHCl3 (20 mL) was added at 0-5 C to a solution of chloromethylsulfonyl chloride (3 g, 20 mmol) in CHCl3 (20 mL). The reaction mixture was stirred at that temperature for 20 min, warmed to room temperature,and stirred for 1 h. It was then washed with water(2×30 mL) and dried over MgSO4, the solvent was evaporated, and the product was recrystallized from CHCl3-hexane mixture. 4-(Chloromethylsulfonyl)morpholine (2d). The yield was 3.11 g (78%), colorless crystals, m.p. 69-71 C (cf. Ref. 11: 70.5-71 C(EtOH)). IR, /cm-1: 3016, 2976, 2844, 1456, 1348 (SO2), 1264,1160 (SO2), 1104, 956, 748. 1H NMR (CDCl3),: 3.48 (t, 4 H,CH2NCH2, J = 4.4 Hz); 3.77 (t, 4 H, CH2OCH2, J = 4.4 Hz);4.55 (s, 2 H, CH2Cl).

References:

Kalugin;Shestopalov [Russian Chemical Bulletin,2019,vol. 68,# 2,p. 357 - 364][Izv. Akad. Nauk, Ser. Khim.,2019,# 2,p. 357 - 364,8]