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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence