Ethanol → HCID 16112965, Verbindung

HRID 30591Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 30591
[F:1][CH:2]([F:21])[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]=[C:15](O)C=2)=O)=[CH:6][CH:5]=1.Cl.[CH3:23][NH:24][C:25]([NH2:27])=[NH:26].[C:28](=[O:31])([O-])[O-].[Na+].[Na+].C([OH:36])C>>[NH2:26][C:25]1[N:24]([CH3:23])[C:28](=[O:31])[C:10]([C:7]2[CH:6]=[CH:5][C:4]([O:3][CH:2]([F:1])[F:21])=[CH:9][CH:8]=2)([C:11]2[CH:13]=[CH:18][CH:17]=[C:16]([OH:36])[CH:15]=2)[N:27]=1

Komponenten

5

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 59790334HCID 59790334, VerbindungHCID 178485118HCID 178485118, Verbindung

Produkt 1

HCID 16112965HCID 16112965, Verbindung

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customevaporated in vacuo
  3. customThe resultant residue was partitioned between water and chloroform
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. customevaporated to a light brown oil
  7. customThe oil was purified by flash chromatography (silica gel)
  8. washstep gradient elution (100% chloroform to 15% methanol/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-04fbf9e34c2148a28f4e292ac19fa6d2
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423158B2

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