Water → HCID 72760486, compound

Temperature

10 °C

N-Chlorosuccinimide (NCS) (421.2 g, 3.15 mol) was suspended in dimethylformamide (DMF) (499.4 g) and cooled to about 10° C. The oxime solution in toluene (3.15 mol) was added slowly over at least 2 h with sufficient cooling to maintain the reaction temperature between 10-25° C. (The reaction is exothermic, but heat evolution is not immediate. Initially small amounts of the oxime solution (about 5%) were added. Once heat evolution began, the remainder of the solution was added). After complete addition of the oxime, the mixture was stirred at 15-25° for at least 30 min. Purified water (1050 g) was added slowly (slight exothermic) over 15 min while maintaining the temperature at 10-30° C. The two-phase mixture was stirred for 15 min. at 15-25° C. and the layers were separated. The water layer was discarded and the organic layer washed with purified water (3×1050 g). The organic layer containing the chlorooxime was isolated and used in the next step without further purification. (The solution is lachrymator).

1. temperaturewith sufficient cooling
2. temperatureto maintain the reaction temperature between 10-25° C. (The reaction
3. temperatureheat evolution
4. additionthe remainder of the solution was added)
5. temperaturewhile maintaining the temperature at 10-30° C
6. stirringThe two-phase mixture was stirred for 15 min. at 15-25° C.
7. customthe layers were separated
8. washthe organic layer washed with purified water (3×1050 g)
9. additionThe organic layer containing the chlorooxime
10. customwas isolated
11. customused in the next step without further purification

ORD record

ord-c16cdf88e8194aed89933ed2ab102ea5

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06576786B2