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Dichloromethane → HCID 69849532, Verbindung

HRID 393154
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 393154
[CH3:1][CH:2]([CH3:24])[CH:3]([NH:14][CH2:15][CH2:16][NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:4]1[C:5]([C:10]([F:13])([F:12])[F:11])=[N:6][CH:7]=[N:8][CH:9]=1.C(N(CC)CC)C.ClCCl.[C:35](Cl)(Cl)=[O:36]>O>[CH3:1][CH:2]([CH3:24])[CH:3]([N:14]1[CH2:15][CH2:16][N:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:35]1=[O:36])[C:4]1[C:5]([C:10]([F:12])([F:11])[F:13])=[N:6][CH:7]=[N:8][CH:9]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6344Dichloromethane2×HCID 6371PhosgeneHCID 8471TriethylamineHCID 22648755HCID 22648755, Verbindung

Produkt 1

HCID 69849532HCID 69849532, VerbindungAusbeute 68,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

1.05 g (4.2 mol) of 5-(1-chloro-2-methylpropyl)-4-trifluoromethylpyrimidine and 0.61 (4.2 mol) of N-phenylethylenediamine were added to 10 ml of isopropyl alcohol, followed by stirring at room temperature for 6 hours. After completion of the reaction, the reaction solution was concentrated, then poured into water and extracted with ethyl acetate, and purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1 to ethyl acetate) to obtain 0.38 g of N-[2-methyl-1-(4-trifluoromethylpyrimidin-5-yl)-propyl]-N′-phenylethane-1,2-diamine. Then, 0.38 g (1 mmol) of N-[2-methyl-1-(4-trifluoromethylpyrimidin-5-yl)-propyl]-N′-phenylethane-1,2-diamine and 0.5 g (5 mmol) of triethylamine were added to 10 ml of dichloromethane, and a dichloromethane solution containing 0.2 g (2 mmol) of phosgene was dropwise added under cooling with ice. After the dropwise addition, stirring was further continued at room temperature for 1 hour to terminate the reaction. After termination of the reaction, the product was poured into water, washed with an aqueous sodium hydrogencarbonate solution, dried and concentrated, and the obtained oily product was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1 to ethyl acetate) to obtain 0.25 g (yield: 61%) of 1-[2-methyl-1-(4-trifluoromethyl-pyrimidin-5-yl)-propyl]-3-phenylimidazolin-2-one as colorless crystals (melting point: 126-128° C.).

Aufarbeitung

  1. additionwas dropwise added
  2. temperatureunder cooling with ice
  3. additionAfter the dropwise addition
  4. customto terminate
  5. customthe reaction
  6. customAfter termination of the reaction
  7. washwashed with an aqueous sodium hydrogencarbonate solution
  8. customdried
  9. concentrationconcentrated
  10. customthe obtained oily product was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1 to ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-0a71339639754f2bb4bf12f6cf184d9d
Quelldatensatz
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06806230B1

Notizen zur Reaktion

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