Aniline → Chloroacetanilide

Participants

Reaction Steps

To a solution of aniline (1 mL, 11 mmol) and CH2Cl2 (150 mL), pyridine (886 mL, 1 mmol) was added. Then 2-chloroacetyl chloride (872 mL, 11 mmol) was added dropwise over 10 min. After the addition was complete, the mixture was reacted at room temperature for 2 hours. The reaction was then quenched with water (100 mL), the layers were separated and the aqueous layer was extracted with CH2Cl2 (2×50 mL). The combined organic layer was washed water, brine, and dried over Na2SO4. The solvent was evaporated to give a colorless solid (1.7 g, 91% yield). The crude product was directly used for next step. 1H NMR (CDCl3, 400 MHz) δ 8.25 (br s., 1H), 7.57 (d, J=7.6 Hz, 2H), 7.39 (t, J=7.6 Hz, 2H), 7.20 (t, J=7.4 Hz, 1H), 4.22 (s, 2H).

Provenance & Evidence