Phosphorus oxychloride → HCID 21557075, compound

HRID 267367Notes

Reaction equation

HRID 267367 reaction equation
P(Cl)(Cl)([Cl:3])=O.O[C:7]1[C:12]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][N:10]=[CH:9][N:8]=1>>[Cl:3][C:7]1[C:12]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][N:10]=[CH:9][N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178518075HCID 178518075, compound

Product 1

HCID 21557075HCID 21557075, compound

Procedure

To 500 ml. of phosphorus oxychloride was added 85.5 g. (0.455 mol) of 4-hydroxy-5-phenoxy pyrimidine and the suspension heated at 70° in an oil bath. After 1 hr the reaction mixture became homogeneous and after 1.5 hr total reduction time the bulk of the phosphorus oxychloride was removed by distillation at reduced pressure. The residue was slowly added to well stirred iced water and the residual acid was cautiously neutralized with ammonium hydroxide solution to pH 8 and was extracted with 3 × 700 ml. of chloroform. The chloroform extracts were dried over anhydrous sodium sulfate filtered and concentrated in vacuo to 85.7 g. (90%) of a black oil. A colorless oil could be obtained by evaporative distillation of this material at 130° (0.1 mm).

Workup

  1. customtotal reduction time the bulk of the phosphorus oxychloride was removed by distillation at reduced pressure
  2. additionThe residue was slowly added to well stirred iced water
  3. extractionwas extracted with 3 × 700 ml
  4. dry with materialThe chloroform extracts were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to 85.7 g
  7. customA colorless oil could be obtained by evaporative distillation of this material at 130° (0.1 mm)

Sources & evidence

ORD record
ord-2112f0ba8b2e4681bab9c519cf00be07
Source dataset
uspto-grants-1976_03
Patent number
US03941889

Reaction notes

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