Water → 2-Amino-2-[3-(trifluoromethyl)phenyl]ethyl carbamate hydrochloride

Temperature

60 °C

A solution of 1.00 g (3.28 mmol) of a compound from Example 59A in 20 ml of acetonitrile was cooled to −15° C. and admixed with 399 μl (4.59 mmol) of chlorosulphonyl isocyanate. After 10 min, 18 ml of water were added and the mixture was heated at 60° C. for 2 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 this mixture was stirred at RT for 5 min and concentrated on a rotary evaporator. Drying of the residue in an HV gave 785 mg (84% of theory) of the title compound.

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. concentrationconcentrated on a rotary evaporator
6. customDrying of the residue in an HV

ORD record

ord-43cf22877831469fb9c87285a79d8fee

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796324B2