Water → N-Phenyl-N'-(4-(6-phenylaminopyrimidin-4-yloxy)phenyl)urea

HRID 387989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387989
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:8]=2)=[CH:4][CH:3]=1.[C:22]1([N:28]=[C:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[C:22]1([NH:28][C:29]([NH:1][C:2]2[CH:21]=[CH:20][C:5]([O:6][C:7]3[CH:8]=[C:9]([NH:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[N:10]=[CH:11][N:12]=3)=[CH:4][CH:3]=2)=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

7

Edukt 3

HCID 962WaterHCID 7672Phenyl isocyanateHCID 22936405N-(6-(4-Aminophenoxy)pyrimidin-4-yl)phenylamine

Produkt 1

HCID 22936423N-Phenyl-N'-(4-(6-phenylaminopyrimidin-4-yloxy)phenyl)ureaAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

N-(6-(4-Aminophenoxy)pyrimidin-4-yl)phenylamine (55.6 mg, 0.200 mmol) and phenyl isocyanate (26.1 mg, 0.220 mmol) were stirred together in dimethylformamide (1 ml) at room temperature for 12 hours. The reaction solution was distributed between ethyl acetate and water, the organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was suspended in ethyl acetate, the suspension was diluted with hexane, and the crystals were filtered out, washed with hexane and then blow-dried to obtain the title compound (69.0 mg, 0.174 mmol, 87%) as colorless crystals.

Aufarbeitung

  1. washthe organic layer was washed with water and saturated saline
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe drying agent was filtered off
  4. distillationthe filtrate was distilled off under reduced pressure
  5. customThe obtained crude product
  6. filtrationthe crystals were filtered out
  7. washwashed with hexane
  8. customblow-dried

Quellen und Nachweise

ORD-Eintrag
ord-50fe1ed8f3814048b8c94103a3666550
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372981B2

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