Sodium Iodide → 2,4-Dichloro-5-(iodomethyl)pyrimidine

HRID 7225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 7225
[I-:1].[Na+].[Cl:3][C:4]1[N:9]=[C:8]([Cl:10])[C:7]([CH2:11]Cl)=[CH:6][N:5]=1>CC(C)=O>[Cl:3][C:4]1[N:9]=[C:8]([Cl:10])[C:7]([CH2:11][I:1])=[CH:6][N:5]=1

Komponenten

4

Edukt 2

HCID 5238Sodium IodideHCID 135682792,4-Dichloro-5-(chloromethyl)pyrimidine

Produkt 1

HCID 219393522,4-Dichloro-5-(iodomethyl)pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A 500-mL, round-bottom flask equipped with a magnetic stirrer, condenser, and nitrogen-inlet bubbler was charged with sodium iodide (38.5 g, 256.9 mmol) (Aldrich) and acetone (300 mL). After a clear solution was obtained, 2,4-dichloro-5-(chloromethyl)pyrimidine (50.0 g, 253.2 mmol) (from Example 1b supra) was added in one portion. After stirring at room temperature for 20 minutes, the mixture was heated to reflux for 15 minutes. NMR analysis indicated 98% conversion. After cooling to room temperature, the resulting precipitate (sodium chloride) was removed by filtration through a medium-sintered glass funnel and washed with acetone. The combined filtrate and washes were concentrated to a weight of ca. 75 g. The resulting concentrated solution of 2,4-dichloro-5-(iodomethyl)pyrimidine in acetone was diluted with toluene (20 mL). After concentration to a weight of ca.85 g in order to remove the residual acetone, this concentrated solution of 2,4-dichloro-5-(iodomethyl)pyrimidine in toluene was used directly in the next step.

Aufarbeitung

  1. customA 500-mL, round-bottom flask equipped with a magnetic stirrer, condenser, and nitrogen-inlet bubbler
  2. customAfter a clear solution was obtained
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 15 minutes
  5. temperatureAfter cooling to room temperature
  6. customthe resulting precipitate (sodium chloride) was removed by filtration through a medium-sintered glass funnel
  7. washwashed with acetone
  8. concentrationThe combined filtrate and washes were concentrated to a weight of ca. 75 g
  9. additionThe resulting concentrated solution of 2,4-dichloro-5-(iodomethyl)pyrimidine in acetone was diluted with toluene (20 mL)
  10. concentrationAfter concentration to a weight of ca
  11. custom85 g in order to remove the residual acetone

Quellen und Nachweise

ORD-Eintrag
ord-1b16208f64b242d0b74b42e9292d9bec
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084270B2

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