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TERT-BUTYL N-(4-ISOTHIOCYANATOPHENYL)CARBAMATE synthesis

3synthesis methods
-

Yield:89631-75-4 83%

Reaction Conditions:

with triethylamine in tetrahydrofuran at 0 - 20;

Steps:

18.a

To a mixture of tent-butyl-4-aminophenylcarbamate (0.5 g, 2.4 mmol) and triethylamine (0.98 mL, 7.2 mmol) in THF (45 mL) was added dropwise thiophosgene (0.2 mL, 2.64 mmol) at 0° C., and the mixture was stirred at rt for 30 min. The reaction mixture was quenched with water and extracted with ether (2×30 mL). The organic layer was dried over Na2SO4 and concentrated to give 0.5 g (83% yield) of the titled compound, which was used for next step without further purification.1H-NMR (400 MHz, CDCl3) δ (ppm) 1.50 (s, 9H), 6.50 (s, 1H), 7.14 (d, 2H, J=8.6 Hz), 7.34 (d, 2H, J=8.4 Hz). LCMS m/z [M+H]+251.2.

References:

US2010/137386,2010,A1 Location in patent:Page/Page column 29