Dichloromethane → 1-Methoxy-1,3,3-trimethylurea

Temperature

-20 °C

A mixture of dimethylhydroxylamine hydrochloride (150.0 g, 1.54 mol), 4-dimethylaminopyridine (9.4 g, 0.076 mol), and dichloromethane (1.35 L) was chilled to −20° C., under argon. Dimethylcarbamyl chloride (135 ml, 1.46 mol) and pyridine (315 ml) were added consecutively over 25 minutes. The reaction was slowly warmed to room temperature over 2 hours, and agitated for about 16 hours. The reaction mixture was filtered to remove pyridine hydrochloride, and concentrated by rotary evaporator. The mixture was diluted with t-butyl methyl ether (500 ml), and the solids were removed by filtration. The filtrate was concentrated by rotary evaporation. Vacuum distillation provided the desired product (135.10 g, 69%) as a colorless oil.

1. temperatureThe reaction was slowly warmed to room temperature over 2 hours
2. filtrationThe reaction mixture was filtered
3. customto remove pyridine hydrochloride
4. concentrationconcentrated by rotary evaporator
5. additionThe mixture was diluted with t-butyl methyl ether (500 ml)
6. customthe solids were removed by filtration
7. concentrationThe filtrate was concentrated by rotary evaporation
8. distillationVacuum distillation

ORD record

ord-de95aab7108642a585d004ea6ce263c2

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846735B2