Reacción #1904064

Ecuación de reacción

5-(5,5-dimethyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)-1H-pyrrole-2-carbonitrile

Lawesson's reagent

→

title compound

Rendimiento 118.4%

5-(5,5-Dimethyl-2-thioxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)-1H-pyrrole-2-carbonitrile

Rendimiento 118.4%

Disolventes

toluene

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISSOLUTIONto dissolve the starting material)
2. 2
   Temperaturacooled to rt
3. 3
   Concentraciónconcentrated
4. 4
   OtroThe residue was purified by a flash chromatography on silica gel column (hexane:THF/4:1)

Procedimiento

To a solution of 5-(5,5-dimethyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)-1H-pyrrole-2-carbonitrile (0.4 g, 1.4 mmol) in a mixture of toluene (20 mL) and THF (10 mL, help to dissolve the starting material) was added at rt under nitrogen the Lawesson's reagent (0.29 g, 0.71 mmol). The mixture was heated at 100° C. for 10 minutes, cooled to rt, and concentrated. The residue was purified by a flash chromatography on silica gel column (hexane:THF/4:1) to give the title compound as a yellowish solid (0.25 g, 60%). 1H-NMR (DMSO-d6) δ 12.66 (s, 1H), 11.96 (s, 1H), 7.69 (d, J=1.49 Hz, 1H), 7.64 (dd, J=1.48, 8.44 Hz, 1H), 7.35 (d, J=8.51 Hz, 1H), 7.01 (m, 1H), 6.79 (m, 1H), 4.49 (s, 2H), 1.60 (s, 6H); MS (FI) m/z 296 ([M−H]−, 100%)

Fuente