Réaction #58869

Équation de réaction

1-(4-(difluoromethoxy)phenyl)-2-(3-hydroxyphenyl)ethane-1,2-dione

N-methylguanidine hydrochloride

sodium carbonate

ethanol

→

title compound

2-Amino-5-[4-(difluoromethoxy)phenyl]-5-(3-hydroxyphenyl)-3-methyl-3,5-dihydro-4H-imidazol-4-one

Conditions de réaction

Traitement

1. 1
   Températurecooled to room temperature
2. 2
   Autreevaporated in vacuo
3. 3
   AutreThe resultant residue was partitioned between water and chloroform
4. 4
   AutreThe organic phase was separated
5. 5
   Séchagedried over Na2SO4
6. 6
   Autreevaporated to a light brown oil
7. 7
   AutreThe oil was purified by flash chromatography (silica gel)
8. 8
   Lavagestep gradient elution (100% chloroform to 15% methanol/chloroform)

Mode opératoire

A mixture of 1-(4-(difluoromethoxy)phenyl)-2-(3-hydroxyphenyl)ethane-1,2-dione (2.75 g), N-methylguanidine hydrochloride (1.237 g) and sodium carbonate (2.20 g) in ethanol was heated at 85° C. for 8 h, cooled to room temperature and evaporated in vacuo. The resultant residue was partitioned between water and chloroform. The organic phase was separated, dried over Na2SO4 and evaporated to a light brown oil. The oil was purified by flash chromatography (silica gel) using step gradient elution (100% chloroform to 15% methanol/chloroform) to afford the title compound as a white foamy glass, 2.20 g; 1H NMR (DMSO-d6): δ 9.24 (bs, 1H), 7.42 (d, J=8.8 Hz, 2H), 7.12 (t, J=74.3 Hz, 1H), 7.06 (d, J=8.8 Hz, 2H), 7.02 (m, 1H), 6.80 (m, 2H), 6.57 (bs, 2H), and 6.56 (m, 1H); MS (APPI) m/z 348.

Source