(4-Aminophenoxy)benzene → HCID 21025113, Verbindung

HRID 1796596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1796596
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:18])=[C:8]2[C:13](Cl)=[C:12]([C:15]#[N:16])[CH:11]=[N:10][N:9]2[CH:17]=1)=[O:5])[CH3:2].C([O-])([O-])=O.[K+].[K+].[O:25]([C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C.ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:18])=[C:8]2[C:13]([NH:36][C:35]3[CH:34]=[CH:33][C:32]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:38][CH:37]=3)=[C:12]([C:15]#[N:16])[CH:11]=[N:10][N:9]2[CH:17]=1)=[O:5])[CH3:2]

Komponenten

6

Edukt 3

HCID 8764(4-Aminophenoxy)benzeneHCID 11430Potassium CarbonateHCID 21025099HCID 21025099, Verbindung

Produkt 1

HCID 21025113HCID 21025113, VerbindungAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of compound 1D (26 mg, 0.10 mmol) in DMF (2 mL) were added K2CO3 (138 mg, 1.00 mmol) and p-phenoxyaniline (20 mg, 0.11 mmol) at 25° C. The reaction mixture was stirred for 12 h and then diluted with dichloromethane (15 mL) and washed with water (10 mL) and brine (10 mL). The organic phase was dried over Na2SO4 and concentrated and the resulting residue was triturated with methanol to afford 31 mg (76% yield) of the desired compound as a yellow solid. HPLC: 100% at 4.62 min (retention time) (YMC S5 ODS column, 4.6×50 mm, eluting with 10-90% aqueous methanol over 4 min containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 413.12 [M+H]+.

Aufarbeitung

  1. washwashed with water (10 mL) and brine (10 mL)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customthe resulting residue was triturated with methanol

Quellen und Nachweise

ORD-Eintrag
ord-6e264df2306845b7a5cdf27995abbd15
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07030112B2

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