Phosphorus oxychloride → 4-Chloro-6-ethyl-5-iodopyrimidine

HRID 129475

Reaction equation

HRID 129475 reaction equation
O[C:2]1[C:7]([I:8])=[C:6]([CH2:9][CH3:10])[N:5]=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:2]1[C:7]([I:8])=[C:6]([CH2:9][CH3:10])[N:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychloride2×HCID 1784377446-ethyl-5-iodo-1H-pyrimidin-4-one

Product 1

HCID 109784874-Chloro-6-ethyl-5-iodopyrimidine

Conditions

Temperature
60 °C

Procedure

21.7 g (0.087 mol) of 4-hydroxy-5-iodo-6-ethylpyrimidine are stirred into 50 ml of phosphorus oxychloride which has been heated to 60° C., a slightly exothermic reaction taking place. The temperature is kept constant at 60° C. and the mixture is left for one hour to complete the reaction. The mixture is then poured onto ice-water and stirred for 30 minutes in order to hydrolyse completely the excess phosphorus oxychloride. Extraction with ethyl acetate yields 23.5 g of crystalline crude product. Recrystallisation from a mixture of 1 part ethyl acetate and 10 parts hexane yields 18.8 g (80.7% of the theoretical yield) of pure substance; m.p. 56°-57° C.

Workup

  1. customa slightly exothermic reaction
  2. customis kept constant at 60° C.
  3. customthe reaction
  4. additionThe mixture is then poured onto ice-water
  5. extractionExtraction with ethyl acetate

Sources & evidence

ORD record
ord-dc2d2da3e86a46dfb1b8ea1d9644cca0
Source dataset
uspto-grants-1995_11
Patent number
US05468751

Linked notes

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