Reacción #677077

Ecuación de reacción

4-ethynylaniline

m-tolyl isocyanate

→

1-(4-ethynylphenyl)-3-(3-methylphenyl)urea

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was then partitioned between EtOAc and aq NH4Cl
2. 2
   OtroThe organic layer was isolated
3. 3
   Lavadowashed with saturated aq NaHCO3, brine
4. 4
   Secadodried with anhydrous sodium sulfate
5. 5
   OtroThe upper solvent layer was decanted
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe resulting solid residue was chromatographed initially with EtOAc-Hex from 1:100 to 1:4
8. 8
   OtroThe product fractions were collected
9. 9
   Concentraciónconcentrated
10. 10
    Otrothe white solid was triturated with EtOAc-Hex (2:1) at room temperature for 18 h
11. 11
    FiltraciónUpon filtration

Procedimiento

To a solution of 4-ethynylaniline (1.308 g, 11.18 mmol, 1 eq) in anhydrous THF (20 mL) under nitrogen atmosphere at room temperature was added dropwise m-tolyl isocyanate (1.684 mL, 1.2 eq). The yellow reaction solution was stirred at room temperature for 3 hours. The reaction was then partitioned between EtOAc and aq NH4Cl. The organic layer was isolated, washed with saturated aq NaHCO3, brine, and dried with anhydrous sodium sulfate. The upper solvent layer was decanted and concentrated. The resulting solid residue was chromatographed initially with EtOAc-Hex from 1:100 to 1:4 and then continued with an eluent from dichloromethane to MeOH-DCM 1:10. The product fractions were collected, concentrated, and the white solid was triturated with EtOAc-Hex (2:1) at room temperature for 18 h. Upon filtration, 1-(4-ethynylphenyl)-3-(3-methylphenyl)urea was obtained as white solid in amount of 2.134 g.

Fuente