4-Bromobutyryl chloride → N-Methyl-N-(4-bromobutyryl)acrylamide

Participants

Reaction Steps

In a nitrogen glove bag 7.27 g (0.05 mole) of N-methyl-N-trimethylsilylacrylamide was placed in a one-necked flask. The flask was fitted with an additional funnel topped with a drying tube. With the flask contents cooled to ice/water temperatures, 9.28 g (0.05 mole) of 4-bromobutyryl chloride was added dropwise through a dropping funnel to the flask over a period of half an hour. The resulting yellow clear mixture was stirred for an additional two hours. The disappearance of the acyl chloride carbonyl band (1800 cm-1) and the increase in intensity of the product amide band (1670 cm-1) was monitored by IR. The by-product trimethylsilyl chloride was removed in vacuo to give 13 g of product. It was used in the next step without further purification.

Provenance & Evidence