반응 #940062

반응 방정식

3-[1,3]dioxolan-2-yl-phenylamine

pyridine

acetyl chloride

→

N-(3-[1,3]dioxolan-2-yl-phenyl)-acetamide

수율 90.0%

용매

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   기타was then brought to room temperature
2. 2
   workup.ADDITIONpoured onto ice-water (60 mL)
3. 3
   기타The phases were separated
4. 4
   세척the organic layer washed with water, saturated NaHCO3, brine
5. 5
   건조dried with MgSO4
6. 6
   기타Removal of the solvent in vacuo

실험 절차

A solution of acetyl chloride (3.75 g, 0.048 mol, 3.4 mL) in CH2Cl2 (6.5 mL) was added dropwise over 15 min to an ice-bath chilled solution of 3-[1,3]dioxolan-2-yl-phenylamine (7.18 g, 0.043 mol) and pyridine (3.40 g, 0.043 mol, 3.5 mL) in CH2Cl2 (85 mL). The solution was then brought to room temperature, stirred for 1 hr, and poured onto ice-water (60 mL). The phases were separated, and the organic layer washed with water, saturated NaHCO3, brine and dried with MgSO4. Removal of the solvent in vacuo afforded N-(3-[1,3]dioxolan-2-yl-phenyl)-acetamide (8.01 g, 90%). 1H NMR (CDCl3) δ 2.08 (s, 3H), 4.03 (d of mult., ethylenedioxy), 5.71 (s, 1H), 7.17 (d, J=8 Hz, 1H), 7.26 (t, J=8 Hz, 1H), 7.53 (d, J=8 Hz, 1H), 7.62 (s, 1H), 8.32 (br s, 1H). 13C NMR (CDCl3) δ 168.9, 138.8, 138.3, 129.1, 122.3, 120.8, 118.1, 103.5, 65.4, 24.4.

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