반응 #7123

반응 방정식

cis-2-aminocyclohexanecarboxylic acid amide

triethylamine

4-chlorobenzenesulfonyl chloride

→

cis-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide

수율 45.1%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   세척washed with H2O, 1.0 M HCl, brine
2. 2
   건조dried over Na2SO4
3. 3
   기타Further purification by flash chromatography (silica gel, 1% to 10% MeOH/CHCl3)

실험 절차

To a solution of cis-2-aminocyclohexanecarboxylic acid amide (2.0 g, 14.0 mmol), and triethylamine (3.9 mL, 28 mmol) in dichloromethane (100 mL) was added 4-chlorobenzenesulfonyl chloride (2.95 g, 14.0 mmol). The resulting solution was stirred at room temperature for 18 h. The reaction was then diluted with dichloromethane (200 mL) and washed with H2O, 1.0 M HCl, brine, and dried over Na2SO4. Further purification by flash chromatography (silica gel, 1% to 10% MeOH/CHCl3) afforded cis-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide (2.0 g) as a white solid in 45% yield over three steps: 1H NMR (DMSO-d6) δ 7.82 (m, 2 H), 7.63 (m, 2 H), 7.56 (d, 1 H, J=7.0 Hz), 7.22 (s br, 1 H), 6.80 (s br, 1 H), 3.43 (m, 1 H), 2.37 (m,1 H), 1.72 (m, 2 H), 1.45 (m, 3 H), 1.15 (m, 3 H); MS m/e 317.05 (M+H)+.

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