Hydrochloric Acid → N,O-dimethacryloylhydroxylamine

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Reaction Steps

N,O-dimethacryloylhydroxylamine was prepared by the reaction of hydroxylamine with methacryloyl chloride in pyridine medium. Hydroxylamine hydrochloride (10 g; 0.144 mol) was dissolved in 50 ml pyridine (0.632 mol) and 25.4 g (0.243 mol) methacryloyl chloride was dropwise added. Temperature of the reaction mixture was kept below 45° C. After completed addition of methacryloyl chloride, the mixture was stirred at ambient temperature for 2 hours. Then, the mixture was diluted with 100 ml chloroform and 21 ml hydrochloric acid (0.245 mol) was slowly dropwise added in order to transfer pyridine to its hydrochloride. The organic layer was separated, washed four times with 100 ml water, and then dried over MgSO4. Chloroform was evaporated in vacuum and the oily residue was dried in vacuum of an oil pump. The product crystallized during drying, the crystals were filtered and twice recrystallized from the mixture diethyl ether-light petroleum. The yield was 7.0 g (34%) N,O-dimethacryloylhydroxylamine, m.p. 55° C., elemental analysis: calculated C--56.70, H--6.55, N--8.28%; found C--56.74, H--6.22, N--8.34%.

Provenance & Evidence