Phosphorus oxychloride → HCID 59511172, compound

HRID 1157323Notes

Reaction equation

HRID 1157323 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:19][NH:18][C:17](=O)[CH:16]=2)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:30])=O>>[Cl:30][C:17]1[N:18]=[N:19][C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:15]([N:12]2[CH2:13][CH2:14][N:9]([C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:8])[CH2:10][CH2:11]2)[CH:16]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 14909614HCID 14909614, compound

Product 1

HCID 59511172HCID 59511172, compound

Conditions

Temperature
80 °C

Procedure

To 5-(4-benzoylpiperazin-1-yl)-6-phenylpyridazin-3(2H)-one (1.3 g) taken in single necked round bottom flask, phosphorusoxychloride (10 ml) was added and the mixture was heated to 80° C. for 4 hrs. Reaction mixture was cooled to room temperature and concentrated to remove excess phosphorus oxychloride. Residue was slowly poured into ice and neutralized with solid sodium bicarbonate. The mixture was extracted with Ethyl acetate (3×100 ml). The combined organic layer was dried over anhydrous sodium sulphate and concentrated to afford (4-(6-chloro-3-phenylpyridazin-4-yl)piperazin-1-yl)(phenyl)methanone as white solid.

Workup

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. concentrationconcentrated
  4. customto remove excess phosphorus oxychloride
  5. additionResidue was slowly poured into ice and neutralized with solid sodium bicarbonate
  6. extractionThe mixture was extracted with Ethyl acetate (3×100 ml)
  7. dry with materialThe combined organic layer was dried over anhydrous sodium sulphate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d6eb4ecec83a4f2cba61c1514f64c2b4
Source dataset
uspto-grants-2010_10
Patent number
US07807671B2

Reaction notes

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