Formic Acid → HCID 58234155, compound

Participants

Reaction Conditions

Reaction Steps

A 5-liter four-necked flask equipped with a thermometer, a dropping funnel and a stirrer was purged with nitrogen, and 980 g of heptane and 334 g (2.4 mol) of chlorosulfonyl isocyanate were added thereto using the dropping funnel. The internal temperature was cooled to 5° C., and 110 g (2.4 mol) of formic acid was added dropwise from the dropping funnel at a rate that maintained the temperature inside the flask at 5 to 8° C. Following completion of the dropwise addition, the internal temperature was raised to 20° C., and the mixture was stirred for 10 hours. To the resulting mixed solution was added a solution containing 186.7 g (0.79 mol) of 3-hydroxyadamantyl methacrylate, 525 g of N-methylpyrrolidone, 2.1 g of 4-methoxyphenol and 2.1 g of phenothiazine, with the addition performed via the dropping funnel at a rate that maintained the temperature inside the flask at a temperature of not more than 20° C. Following stirring for 3 hours at an internal temperature of 20 to 25° C., the reaction mixture was transferred to a separating funnel, and the upper layer was discarded. To the thus obtained lower layer were added 890 g of ethyl acetate and 700 g of water, and the resulting mixture was stirred, and left to settle. Then, the resultant was subjected to liquid separation to extract the ethyl acetate phase and the aqueous phase. A further 890 g of ethyl acetate was then added to the water layer, and a second extraction was performed. Following mixing of the two ethyl acetate layers, the resulting solution was washed 5 times with 900 g of water. The washed solution was then washed with 400 g of a 7% by weight aqueous solution of sodium bicarbonate, and then 400 g of water. The this obtained washed organic layer was concentrated under reduced pressure to obtain a concentrated solution of 500 g, and 630 g of toluene was added. The resulting solution was then heated to an internal temperature of 55° C., and then cooled to 3° C. to effect a recrystallization. The suspension obtained by the recrystallization was filtered, thereby obtaining 159.5 g (0.51 mol) (yield=64%) of crystals of the objective compound (11).

Provenance & Evidence