Hydrogen iodide → HCID 90014635, Verbindung

HRID 2207691Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2207691
Cl[C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[N:3]=1.[IH:19]>C(Cl)Cl>[I:19][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[N:3]=1

Komponenten

4

Edukt 2

HCID 24841Hydrogen iodideHCID 574686142-Chloro-4-methyl-6-(4-trifluoromethyl-phenyl)-pyrimidine

Produkt 1

HCID 90014635HCID 90014635, VerbindungAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-chloro-4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidine (which may be prepared as described in Description 5) (167.5 g, 614.34 mmol) in DCM (1325 mL) was added HI (57% in water) (405.23 mL, 3071.7 mmol) dropwise. The reaction was then stirred at room temperature overnight. Additional DCM (500 mL) was added, and the reaction was filtered. The solid was dried then transferred into a beaker containing water (1 L) and EtOAc (1.25 L). The aqueous was basified to pH 10 with K2CO3, and the layers were stirred until all the solid dissolved. Sodium metabisulfite (8.75 g) was added and the layers were stirred until all solid dissolved. The layers were separated, and the aqueous was re-extracted with EtOAc (200 mL). The combined organics were then dried over MgSO4, filtered and concentrated in vacuo to give the title material (D6) (205.68 g, 564.9 mmol, 92% yield) as a pale orange solid. NMR indicated this was >95% pure.

Aufarbeitung

  1. filtrationthe reaction was filtered
  2. customThe solid was dried
  3. additioncontaining water (1 L) and EtOAc (1.25 L)
  4. stirringthe layers were stirred until all the solid
  5. dissolutiondissolved
  6. additionSodium metabisulfite (8.75 g) was added
  7. stirringthe layers were stirred until all solid
  8. dissolutiondissolved
  9. customThe layers were separated
  10. extractionthe aqueous was re-extracted with EtOAc (200 mL)
  11. dry with materialThe combined organics were then dried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bcd8c898f47c4e7cb418ac2b6effadb7
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376445B2

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