Acetyl chloride → 2-Methyl-4-benzoxazolecarboxamide

Participants

Reaction Steps

To a solution of the methyl (2-amino-3-hydroxy)-benzoate (3 g; 18.01 mM) in m-xylene (150 ml) was added acetyl chloride (1.518 ml; 21.6 mM). A precipitate was formed; this was left to stir for 30 minutes. On the addition of triethylamine (2.97 ml; 21.6 mM) the solution became translucent. Pyridinium-p-toluene sulphonic acid (1.2 g; 21.6 mM) was added, and the mixture refluxed for 34 hours. The solvent was removed by distillation (vacuum) to yield a brown solid which was column chromatographed (50% ethyl acetate/50% petrol 60/80) to give the desired product as a yellow solid. T.L.C. As above. 1HNMR :200 MHz; CDCl3 ; δ: 2.69(3H;s;2--CH3); 3.99(3H;s;OMe); 7.33(3H;t;H6); 7.63(1H;dd;H7); 7.94(1H;dd;H5).

Provenance & Evidence