Diethyl Ether → 4'-Dimethylaminoacetanilide

Participants

Reaction Steps

To a solution of acetic anhydride (11.5 mL, 12.45 g, 0.122 mol) in anhydrous CH2Cl2 (100 mL) was added N,N-dimethyl-1,4-phenylenediamine (11.37 g; 83.5 mmol) portion-wise over 30 min at 0° C. The mixture was allowed to gradually warm to room temperature and stirred for 24 hours. The solvent was removed under high vacuum to obtain a black residue which was stirred with Et2O (20 mL) at room temperature. The suspension was filtered and the solid washed with Et2O (3×20 mL). The solid residue was dried under high vacuum to obtain the intermediate N-acetyl-N′,N′-dimethyl-1,4-phenylenediamine as a black solid (12.8 g, 86%) which was used in the next step without further purification.

Provenance & Evidence