Thionyl Chloride → HCID 11268205, compound

Participants

Reaction Conditions

Reaction Steps

Preparation of 5-(aziridin-1-yl)-N-(2,3-dihydroxypropyl)-2-(methylsulfonyl)-4-nitrobenzamide (10) A mixture of 5-chloro-2-(methylsulfonyl)-4-nitrobenzoic acid (Somani et al., Br. J. Cancer 1994, 69 (Suppl. XXI), 38) (2.21 g, 7.9 mmol) and SOCl2 (20 mL) containing DMF (2 drops) was refluxed for 1 h, then evaporated to dryness under reduced pressure. The resulting crude acid chloride was dissolved in anhydrous Me2CO (40 mL), and the solution was cooled to −5° C. and treated in one portion with a cold solution of 3-aminopropane-1,2-diol (1.48 g, 1.62 mmol) in water (20 mL). The mixture was shaken at room temperature for 15 min, then diluted with water (20 mL) and concentrated under reduced pressure to ca. 30 mL. After addition of solid NaCl, the mixture was extracted with EtOAc (3x), and the extracts were worked up to give a solid. This was dissolbed in EtOAc and filtered through a column of silica gel to give 5-chloro-N-(2,3-dihydroxypropyl)-2-(methylsulfonyl)-4-nitrobenzamide (2.54 g, 91%), mp (EtOAc/iPr2O) 141-142° C. 1NMR [(CD3)2SO] δ8.83 (t, J=5.7 Hz, 1H, NH), 8.55 (s, 1 , H-3), 8.08 (s, 1H, H-6), 4.81 (d, J=5.0 Hz, 1H, CHOH), 4.55 (t, J=5.8 Hz, 1H, CH2OH), 3.70-3.58 (m, 1H, CHOH), 3.45 (s, 3H, CH3), 3.44-3.35 (m, 3H, CH2OH & CONHCHH), 3.17-3.06 (m, 1H, CONHCHH). Anal. Calcd for C11H13ClN2O7S: C, 3 71; N, 7.94; S, 9.09 Found: C, 37.73;H, 3.96; N, 7.83; S, 9.29%.

Provenance & Evidence