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Acetyl chloride → HCID 178474038, Verbindung

HRID 2205816
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2205816
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[C:11]([NH2:13])[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.CN1CC[O:18][CH2:17][CH2:16]1.C(Cl)(=O)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[C:11]([NH:13][C:17](=[O:18])[CH3:16])[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 79724-MethylmorpholineHCID 178507283HCID 178507283, Verbindung

Produkt 1

HCID 178474038HCID 178474038, VerbindungAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-(3-fluorophenyl)-1H-pyrazol-5-amine (6.5 g, 36 mmol) and N-methylmorpholine (9.7 mL, 88 mmol) in CH2Cl2 (150 mL) was added acetyl chloride (6 mL, 85 mmol) dropwise at 0° C. under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature for 1 d. The reaction mixture was concentrated in vacuo. MeOH (50 mL) and THF (50 mL) were added to the residue, followed by the addition of NaOH solution (aq. 2.5 M, 42.5 mL) at 0° C. The reaction mixture was stirred at room temperature for 15 min and HCl solution was added until pH reached ˜6. The organic solvents were evaporated in vacuo. The solid from the resulting aqueous suspension was collected by filtration, yielding the title compound as a solid (7.6 g).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionMeOH (50 mL) and THF (50 mL) were added to the residue
  3. additionfollowed by the addition of NaOH solution (aq. 2.5 M, 42.5 mL) at 0° C
  4. stirringThe reaction mixture was stirred at room temperature for 15 min
  5. additionHCl solution was added until pH
  6. customThe organic solvents were evaporated in vacuo
  7. filtrationThe solid from the resulting aqueous suspension was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-962ba44ff07f44a5a876dd62f68038b1
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09371332B2

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