Triethylamine → HCID 17963842, compound

Temperature

-30 °C

To a solution of 3-iodo-5-(trifluoromethyl)benzoic acid (2.32 g) and triethylamine (1.13 ml) in dichloromethane (20 ml) was added dropwise a solution of ethyl chloroformate (1.4 ml) in dichloromethane (2.0 ml) over 10 minutes at −30° C., and the mixture was stirred at −30° C. for 1 hour. 2-Amino-2-methyl-1-propanol was added dropwise to the mixture over 5 minutes at −30° C., and the mixture was stirred at −30° C. for 30 minutes and then at room temperature for 1 hour. The mixture was quenched with aqueous ammonium chloride solution at 0° C., and extracted with dichloromethane (X2). The combined organic extracts were washed successively with saturated aqueous sodium hydrogen carbonate solution, 1N hydrochloric acid and brine, and then dried over magnesium sulfate, evaporated, and purified with column chromatography (silica gel, ethyl acetate:hexane=20:80) to give N-(2-hydroxy-1,1-dimethylethyl)-3-iodo-5-(trifluoromethyl)benzamide (2.10 g) as an oil.

1. stirringthe mixture was stirred at −30° C. for 30 minutes
2. waitat room temperature for 1 hour
3. customThe mixture was quenched with aqueous ammonium chloride solution at 0° C.
4. extractionextracted with dichloromethane (X2)
5. washThe combined organic extracts were washed successively with saturated aqueous sodium hydrogen carbonate solution, 1N hydrochloric acid and brine
6. dry with materialdried over magnesium sulfate
7. customevaporated
8. custompurified with column chromatography (silica gel, ethyl acetate:hexane=20:80)

ORD record

ord-84078714ba7a464d93a776d250321bd5

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07166598B2