Sodium Carbonate → HCID 57435849, compound

HRID 30546Notes

Reaction equation

[F:1][CH:2]([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15]C=2)=O)=[CH:6][CH:5]=1.[O:21]1[CH2:26]COCC1.Cl.[CH3:28][NH:29][C:30]([NH2:32])=[NH:31].C([O-])([O-])=O.[Na+].[Na+]>O.CCO>[NH2:32][C:30]1[N:29]([CH3:28])[C:26](=[O:21])[C:10]([C:7]2[CH:6]=[CH:5][C:4]([O:3][CH:2]([F:1])[F:20])=[CH:9][CH:8]=2)([C:11]2[CH:13]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:31]=1

Participants

Conditions

Temperature: 95 °C

Procedure

Into a mixture of 1-[4-(difluoromethoxy)phenyl]-2-phenylethane-1,2-dione (3.7 g, 13.4 mmol), dioxane (180 mL) and EtOH (240 mL) were added 1-methylguanidine hydrochloride (6.6 g, 60.3 mmol), and a solution of Na2CO3 (6.4 g, 60.3 mmol) in H2O (20 mL). The new mixture was stirred at 95° C. for 3 hours. Then, the volatiles were removed under vacuum and the residue was taken in water and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification on silica gel (ISCO) using MeOH/EtOAc (1/20) as the eluting solvent gave 2-amino-5-[4-(difluoromethoxy)phenyl]-3-methyl-5-phenyl-3,5-dihydro-4H-imidazol-4-one as a white solid (3.65 g, 94% yield). MS m/e (M+H)+ 332; 1H NMR (400 MHz, DMSO-d6) 2.93 (s, 3H), 6.61 (brs, 2H), 7.1 (d, J=8.54 Hz, 2H), 7.15-7.31 (m, 4H), 7.38 (m, 2H), 7.42 (d, J=8.54 Hz, 2H).

Workup

customThen, the volatiles were removed under vacuum
extractionextracted with EtOAc
dry with materialThe organic extracts were dried over MgSO4
customEvaporation and purification on silica gel (ISCO)

Sources & evidence

ORD record: ord-d5c0ab4c9b4247f1ab127963ddfff5ac
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423158B2

Reaction notes

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