Hydrochloric Acid → HCID 57249691, compound

Temperature

12.5 °C

Sodium hydroxide (117.11 g of a 50% aqueous solution) was added to water (160.5 g), and the solution was cooled to 10-15° C. Tetramethylammonium chloride (4.88 g) was added, followed by the dropwise addition of 1,3-dimethyl 2-(2-fluorophenyl)propanedioate (150 g) over a period of 30 minutes at 10-15° C. The temperature of the reaction was slowly raised to 30° C. after the addition and maintained at 27-32° C. The reaction mass became a thick slurry, and water (25 g) was added to improve stirring. The progress of the reaction was monitored by HPLC. After stirring for 2 hours, the reaction mixture was added to a solution of HCl (231 g) and water (150 mL) over a period of 30 minutes at 5-10° C. The pH of the mixture was adjusted to <2, and the reaction mixture was stirred at 5-10° C. for half an hour. The reaction mixture was then filtered to isolate a solid product that was air dried, and then further dried under reduced pressure at 35° C. for 3 hours. The dried solid was slurried with petroleum ether, and the slurry was filtered to reisolated the solid. The solid was then dried under reduced pressure at 35° C. for 3 hours to give the title product (115.5 g, 93.97%).

1. temperatureThe temperature of the reaction was slowly raised to 30° C.
2. additionafter the addition
3. temperaturemaintained at 27-32° C
4. additionwas added
5. stirringAfter stirring for 2 hours
6. stirringthe reaction mixture was stirred at 5-10° C. for half an hour
7. filtrationThe reaction mixture was then filtered
8. customto isolate a solid product that
9. customdried
10. customfurther dried under reduced pressure at 35° C. for 3 hours
11. filtrationthe slurry was filtered
12. customThe solid was then dried under reduced pressure at 35° C. for 3 hours

ORD record

ord-44f22bd3eb694538a28b182541ea61c1

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09210932B2