Phosphorus oxychloride → HCID 21113078, compound

HRID 1766984Notes

Reaction equation

HRID 1766984 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:17]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[C:11]2[CH:12]=[N:13][NH:14][C:15](=O)[C:10]=2[N:9]=1.O=P(Cl)(Cl)[Cl:27]>>[Cl:27][C:15]1[N:14]=[N:13][CH:12]=[C:11]2[N:17]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])=[N:9][C:10]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 21113074HCID 21113074, compound

Product 1

HCID 21113078HCID 21113078, compound

Procedure

A solution of 2-(2-chloro-phenyl)-1-(4-chloro-phenyl)-1,5-dihydro-imidazo[4,5-d]pyridazin-4-one (I-2g, 22 mg, 0.062 mmol) in POCl3 (3 ml) was heated under reflux for 2.5 hours. The reaction mixture was cooled to room temperature and the solvent was removed under vacuum. The residue was dissolved in toluene and again concentrated. This procedure was repeated twice. The residue was then taken up in CH2Cl2, and H2O was added. The pH of the aqueous solution was adjusted via addition of sat'd aq NaHCO3 until the pH was neutral (˜7). The CH2Cl2 layer was separated and the aqueous solution was extracted with CH2Cl2 (3×). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to give I-2h as a pale yellow oil (22 mg): +APCI MS (M+1) 375.0/377.0; 1H NMR (CDCl3) δ 7.18–7.23 (2H, m), 7.35–7.48 (5H, m), 7.56–7.60 (1H, m), 9.22 (1H, s).

Workup

  1. temperatureunder reflux for 2.5 hours
  2. customthe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in toluene
  4. concentrationagain concentrated
  5. additionH2O was added
  6. additionThe pH of the aqueous solution was adjusted via addition of sat'd aq NaHCO3 until the pH
  7. customThe CH2Cl2 layer was separated
  8. extractionthe aqueous solution was extracted with CH2Cl2 (3×)
  9. dry with materialThe combined organic extracts were dried (Na2SO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-faf074460fe646579988711135c9cd32
Source dataset
uspto-grants-2007_06
Patent number
US07232823B2

Reaction notes

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