Ethanolamine → N-(2-hydroxyethyl)acetoacetamide

Participants

Reaction Conditions

Reaction Steps

Acetonitrile (825 g) and diketene (55.0 g) were introduced into a 5,000 mL four-necked flask, and the mixture was cooled so that the temperature in the flask was lowered to −5 to 0° C. Diketene and 2-aminoethanol were simultaneously added dropwise for 4 hours at a rate of 261.5 g/h and 190 g/h, respectively. In such a case, about 2 hours after the commencement of dropwise addition, the reaction system became uneven, causing stirring difficulty. Therefore, cooled acetonitrile (1,000 g) was further added thereto, and dropwise addition was continued under a suspended state. During the addition, cooling was conducted to maintain the temperature in the flask at −5 to 0° C. Thereafter, 25 g of 2-aminoethanol was added dropwise at a rate of 190 g/h. The resultant was heated to room temperature and aged for 12 hours. Then, while the mixture in the flask was heated to a temperature of 50° C., acetonitrile was removed under reduced pressure, and the resulting mixture was finally kept at a pressure of about 0.001 for 4 hours, to thereby produce about 1,850 g of 2-(acetoacetamido)ethanol.

Provenance & Evidence