Reacción #45767

ord-aa48d38c1d0b4f32810ca3ec04e0401a

Ecuación de reacción

COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1
Lawesson's reagent
Cc1c(-c2ccccc2)c(F)c2oc(C(N)=O)nc2c1C#N
4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxamide
Cc1c(-c2ccccc2)c(F)c2oc(C(N)=S)nc2c1C#N
compound
Rendimiento 41.8%
Cc1c(-c2ccccc2)c(F)c2oc(C(N)=S)nc2c1C#N
4-Cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carbothioamide
Rendimiento 41.8%

Disolventes

Condiciones de reacción

Temperatura
125°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturaby heating
  2. 2
    TemperaturaAfter cooling to room temperature
  3. 3
    Otrothe reaction liquid
  4. 4
    Concentraciónwas concentrated
  5. 5
    Otrothe resulting residue was purified by silica gel column chromatography (eluent, chloroform:ethyl acetate=20:1→10:1)

Procedimiento

Lawesson's reagent (458 mg, 1.13 mmol) was added to a toluene solution of 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-196) (304 mg, 1.03 mmol), followed by heating under reflux in an oil bath at 125° C. for 10 minutes. After cooling to room temperature, the reaction liquid was concentrated, and the resulting residue was purified by silica gel column chromatography (eluent, chloroform:ethyl acetate=20:1→10:1) to obtain the entitled compound (134 mg, 41.8%) as a yellow solid.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07737166B2uspto-grants-2010_06