Triethylamine → N-[[3,5-Bis(trifluoromethyl)phenyl]methyl]-N-methylcarbamic chloride

In 3.0 ml of dichloromethane was dissolved 831 ml of triphosgene, and added dropwise thereto were a solution of 1.08 g of N-(3,5-bistrifluoromethylbenzyl)-N-methylamine and 1.76 ml of triethylamine in 5.0 ml of dichloromethane, spending 10 minutes, under nitrogen atmosphere under ice-cooling. The reaction mixture was stirred at 0° C. to 5° C. for 30 minutes. The solvent was removed by distillation, and the residue was dried. To the residue were added water and dichloromethane and the mixture was extracted twice with dichloromethane. The organic layers were combined and washed with saturated brine, and dried. Then, the solvent was removed by distillation. The residue was purified by silica gel column chromatography (hexane→hexane:ethyl acetate=10:1), to give 760 mg of N-(3,5-bistrifluoromethylbenzyl)-N-methylaminocarbonyl chloride as shown in Table 134 below.

1. additionadded dropwise
2. temperaturecooling
3. customThe solvent was removed by distillation
4. customthe residue was dried
5. additionTo the residue were added water and dichloromethane
6. extractionthe mixture was extracted twice with dichloromethane
7. washwashed with saturated brine
8. customdried
9. customThen, the solvent was removed by distillation
10. customThe residue was purified by silica gel column chromatography (hexane→hexane:ethyl acetate=10:1)

ORD record

ord-9816c3b20ca6408387875aefb739a87d

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07619092B2