Water → 2-Amino-1-[2-(trifluoromethyl)phenyl]ethyl carbamate
Reaction equation
[OH:1][CH:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19])[CH2:3][NH:4]C(=O)OC(C)(C)C.ClS([N:26]=[C:27]=[O:28])(=O)=O.O.C(=O)(O)[O-].[Na+]>C(#N)C>[C:27](=[O:28])([O:1][CH:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:19])([F:20])[F:21])[CH2:3][NH2:4])[NH2:26]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A solution of 420 mg (1.38 mmol) of the compound of Example 36A in 100 ml of acetonitrile was cooled to −15° C., and a solution of 168 μl (1.93 mmol) of chlorosulphonyl isocyanate in 10 ml of acetonitrile was added dropwise. After 5 min, 50 ml of water were added and the reaction mixture was stirred further at 60° C. overnight. After cooling to RT, 50 ml of a saturated aqueous sodium bicarbonate solution were added. The mixture was extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate and freed from the solvent on a rotary evaporator. The residue (321 mg, about 90% pure, 85% of theory) corresponded to the title compound and was reacted further without additional purification.
Workup
- temperatureAfter cooling to RT
- extractionThe mixture was extracted three times with ethyl acetate
- dry with materialThe combined organic phases were dried over sodium sulphate
- customfreed from the solvent on a rotary evaporator
- customwas reacted further without additional purification
Sources & evidence
- ORD record
- ord-e9f7d3ff36ba47e7ad30b8bb048632b0
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09180120B2
Reaction notes
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