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Ethyl Bromide → 2-[N-Ethyl-(5,6,6a,7,8,9-hexahydro-6a-methyl-4H-2-phenalenyl)amino]pyrimidine-5-carboxylic acid

HRID 1097402
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1097402
[H-].[Na+].[CH3:3][C:4]12[C:16]3[C:8](=[CH:9][C:10]([NH:17][C:18]4[N:23]=[CH:22][C:21]([C:24]([O:26]CC)=[O:25])=[CH:20][N:19]=4)=[CH:11][C:12]=3[CH2:13][CH2:14][CH2:15]1)[CH2:7][CH2:6][CH2:5]2.Br[CH2:30][CH3:31].[Cl-].[NH4+]>CN(C)C=O>[CH2:30]([N:17]([C:10]1[CH:9]=[C:8]2[C:16]3[C:4]([CH3:3])([CH2:5][CH2:6][CH2:7]2)[CH2:15][CH2:14][CH2:13][C:12]=3[CH:11]=1)[C:18]1[N:23]=[CH:22][C:21]([C:24]([OH:26])=[O:25])=[CH:20][N:19]=1)[CH3:31]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 25190162HCID 25190162, Verbindung

Produkt 1

HCID 251901592-[N-Ethyl-(5,6,6a,7,8,9-hexahydro-6a-methyl-4H-2-phenalenyl)amino]pyrimidine-5-carboxylic acidAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

A suspension of sodium hydride (60%, 0.008 g) in N,N-dimethylformamide (2 ml) was added with ethyl 2-[(5,6,6a,7,8,9-hexahydro-6a-methyl-4H-2-phenalenyl)amino]pyrimidine-5-carboxylate (0.033 g) dissolved in N,N-dimethylformamide (1 ml), and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was added with bromoethane (0.021 ml), and the mixture was stirred overnight. The reaction mixture was added with saturated aqueous ammonium chloride, and the mixture was extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was suspended in ethanol (5 ml), the suspension was added with 20% aqueous sodium hydroxide (1 ml), and the mixture was stirred at 50° C. for 3 hours. The reaction mixture was left to cool and then made acidic with 2 N aqueous hydrochloric acid, and the mixture was extracted with chloroform. The organic layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was recrystallized from chloroform-n-hexane to obtain the title compound (0.025 g, yield: 76%) as colorless needles (melting point: 257-258° C.).

Aufarbeitung

  1. stirringthe mixture was stirred overnight
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. additionthe suspension was added with 20% aqueous sodium hydroxide (1 ml)
  7. stirringthe mixture was stirred at 50° C. for 3 hours
  8. waitThe reaction mixture was left
  9. temperatureto cool
  10. extractionthe mixture was extracted with chloroform
  11. washThe organic layer was washed successively with water and saturated brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationThe organic layer was concentrated under reduced pressure
  14. customthe resulting residue was recrystallized from chloroform-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-fd20afa952d745969d1d216382fee81a
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08143260B2

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