Chlorine → HCID 131731398, compound

Participants

Reaction Conditions

Reaction Steps

Chlorine was bubbled trough a solution of L(+)-lysine monohydrochloride (150 g, 821 mmol) in HCl (36%) at 70° C. The mixture was irradiated with a medium pressure mercury lamp while stirring. After 2 h the reaction mixture was cooled to 7° C. and a seed crystal was added to induce crystallization. After one hour the resulting crystals were filtered off and the crude product was triturated twice with MeOH. The crystals were collected to afford 4.1 as a white solid. Yield: 12.6 g, 49.7 mmol, 6%. 1H-NMR (300 MHz, DMSO-d6) δ 8.81 (br s, αNH3, 3H), 8.43 (br s, εNH3, 3H), 4.48 (m, γCH, 1H), 3.96 (br s, αCH, 1H), 2.94 (m, εCH2, 2H), 2.31 (m, βCH2+δCH, total 3H), 2.04 (m, δCH, 1H). 13C-NMR (75 MHz, DMSO-d6) δ 169.9 (C═O), 56.6 (γCH), 49.6 (αCH), 38.4 (εCH2), 36.1 (βCH2), 35.1 (δCH2). LC-MS program 3: Rt=1.05 min, MS ES+ (amu): 180.94 [M+H]+.

Provenance & Evidence