Phosphorus oxychloride → 4-Chloro-5-iodo-2,6-dimethylpyrimidine

HRID 129016Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 129016
[CH3:1][C:2]1[N:7]=[C:6](O)[C:5]([I:9])=[C:4]([CH3:10])[N:3]=1.P(Cl)(Cl)([Cl:13])=O>C1(C)C=CC=CC=1>[Cl:13][C:6]1[C:5]([I:9])=[C:4]([CH3:10])[N:3]=[C:2]([CH3:1])[N:7]=1

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178432770HCID 178432770, Verbindung

Produkt 1

HCID 14911174-Chloro-5-iodo-2,6-dimethylpyrimidineAusbeute 93,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 2,6-dimethyl-5-iodo-4-hydroxypyrimidine (24.5 g, 0.098 mol), phosphorus oxychloride (30.0 g, 0.196 mol) and toluene (200 mL) was heated under reflux for 1 h. The mixture was concentrated and ice water (100 mL) was added. The pH was adjusted to 5 with 2.5N NaOH and the mixture was extracted with CH2Cl2. The combined extracts were washed with brine, dried MgSO4), and concentrated to give 24.6 g of a brown solid. The crude product was combined with 26.0 g of similarly prepared material and filtered through a short column of silica gel eluted with CH2Cl2 to give 33.8 g (62%) of product as a yellow solid. An analytical sample was recrystallized from hexane/CH2Cl2, mp 62°-64° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 1 h
  3. concentrationThe mixture was concentrated
  4. additionice water (100 mL) was added
  5. extractionthe mixture was extracted with CH2Cl2
  6. washThe combined extracts were washed with brine, dried MgSO4), and
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0783e2df9f7e42edb55390f2bab0de1e
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466692

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