Phosphorus oxychloride → HCID 13234213, compound

HRID 1995253Notes

Reaction equation

HRID 1995253 reaction equation
[CH:1]([N:4]1[C:8](=[O:9])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[F:17])[NH:6][C:5]1=O)([CH3:3])[CH3:2].P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:5]1[N:4]([CH:1]([CH3:3])[CH3:2])[C:8](=[O:9])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[F:17])[N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychloride2×HCID 13234212HCID 13234212, compound

Product 1

HCID 13234213HCID 13234213, compound

Procedure

4-Isopropyl-1-(4-chloro-2-fluorophenyl)-1,2,4-triazolidine-3,5-dione (6.32 g; 0.023 mol) and phosphorus oxychloride (50 ml) were boiled with stirring for 30 hours. After completion of the reaction, excessive phosphorus oxychloride was removed by distillation under reduced pressure. The separated oily substance was poured into icewater and extracted with chloroform (50 ml) three times. The chloroform layer was washed with a saturated sodium chloride solution until the washings became neutral, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting oily substance was chromatographed on silica gel to give 2.5 g of 3-chloro-4-isopropyl-1-(4-chloro-2-fluorophenyl)-1,2,4-triazolin-5-one.

Workup

  1. customwas removed by distillation under reduced pressure
  2. additionThe separated oily substance was poured into icewater
  3. extractionextracted with chloroform (50 ml) three times
  4. washThe chloroform layer was washed with a saturated sodium chloride solution until the washings
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting oily substance was chromatographed on silica gel

Sources & evidence

ORD record
ord-b090e2d3d65a4d2ab5d201610fff216f
Source dataset
uspto-grants-1983_09
Patent number
US04404019

Reaction notes

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