Ozone → 3-[5-tert-Butyl-3-isoxazolyl]-4-hydroxy-1-methyl-2-imidazolidinone

Participants

Reaction Steps

A 4.74 g. portion of 1-(5-t-butylisoxazol-3-yl)-3-allyl-3-methylurea was dissolved in 50 ml. of methanol, and was cooled to -12°. Ozone-containing air was bubbled through the mixture with good stirring for 80 minutes. The temperature rose as high as 0° during the ozone addition, and the mixture foamed and left solids on the flask walls above the liquid. It was necessary to wash the solid down with 20 ml. of additional methanol. Ten ml. of additional methanol was used to wash the gas frit when it began to plug from precipitated product. After the addition was complete, nitrogen was bubbled through the solution for 5 minutes, and then 1.5 ml. of dimethyl sulfide was added and the mixture was warmed to 20° and diluted with 80 ml. of water. The methanol was removed under vacuum at 40°, and the remaining mixture was filtered and the solids were washed with 50 ml. of water and dried under vacuum at 50° to obtain 2.68 g. of the desired product, m.p. 173°-176°. It was further identified by nmr analysis which showed it to be substantially identical to the product of Example 1.

Provenance & Evidence