Sodium Carbonate → HCID 57435849, Verbindung

HRID 2240924Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2240924
[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

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 57435846HCID 57435846, VerbindungHCID 178485118HCID 178485118, Verbindung

Produkt 1

HCID 57435849HCID 57435849, VerbindungAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

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) δ 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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-819fccb465fd4163ac1aa9d4cebcd99f
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723368B2

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