Water → 2-Amino-2-[2-(trifluoromethyl)phenyl]ethyl carbamate hydrochloride

Temperature

60 °C

A solution of 570 mg (1.87 mmol) of the compound from Example 62A in 100 ml of acetonitrile was cooled to −15° C. and admixed with 325 μl (3.73 mmol) of chlorosulphonyl isocyanate. After 10 min, 50 ml of water were added and the mixture was heated at 60° C. for 4 h. After cooling to RT, the solution was rendered alkaline (pH 9-10) by addition of saturated aqueous sodium hydrogen carbonate solution and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate and freed from the solvents on a rotary evaporator. For complete deprotection of the amino group, the residue was admixed with 15 ml of a 4M solution of hydrogen chloride in dioxane, and the mixture was stirred at RT for 5 min and the volatile components were removed on a rotary evaporator. The residue corresponded to the title compound (630 mg, quant.).

1. temperatureAfter cooling to RT
2. extractionextracted three times with ethyl acetate
3. dry with materialThe combined organic phases were dried over sodium sulphate
4. customfreed from the solvents on a rotary evaporator
5. customthe volatile components were removed on a rotary evaporator

ORD record

ord-68011f39fb0d41bfbd8c63cbddce3552

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796324B2