Phosphorus oxychloride → 105950-89-8

HRID 1586704Notes

Reaction equation

HRID 1586704 reaction equation
O[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][O:9][CH3:10])[N:3]=1.P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][O:9][CH3:10])[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178494677HCID 178494677, compound

Product 1

HCID 14306130105950-89-8

Conditions

Temperature
70 °C

Procedure

47 g (335.7 mmol) of 4-hydroxy-2-methoxymethylpyrimidine (from stage a) are mixed with 210 ml of phosphorus oxychloride and stirred at 70° C. for 2 h and subsequently heated to boiling for 2.5 h. The excess phosphorus oxychloride is removed by distillation in vacuo, the residue is hydrolyzed with ice, and solid potassium bicarbonate is added to eliminate excess acid. Several extractions with methylene chloride are carried out, and the organic phase is evaporated in vacuo. The black residue is filtered through silica gel (n-heptane/ethyl acetate 1:1). 15.7 g of oil are obtained.

Workup

  1. temperaturesubsequently heated
  2. waitto boiling for 2.5 h
  3. customThe excess phosphorus oxychloride is removed by distillation in vacuo
  4. additionis added
  5. extractionSeveral extractions with methylene chloride
  6. customthe organic phase is evaporated in vacuo
  7. filtrationThe black residue is filtered through silica gel (n-heptane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-326fc1cdd1d842e38fb7b997d68f455f
Source dataset
uspto-grants-1993_06
Patent number
US05215990

Reaction notes

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