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Acetyl chloride → HCID 178474038, Verbindung

HRID 1615717
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1615717
[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-58f74570a4e94a0f9cc14af5b9af2610
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08765762B2

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