Phosphorus oxychloride → ST51003135

HRID 350860Notes

Reaction equation

HRID 350860 reaction equation
[C:1]([CH:9]1[C:13](=O)[N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:11]=[C:10]1[CH3:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].P(Cl)(Cl)([Cl:29])=O>>[Cl:29][C:13]1[N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:11]=[C:10]([CH3:21])[C:9]=1[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 976901-Phenyl-3-methyl-4-benzoyl-5-pyrazoloneHCID 516892Sodium Bicarbonate

Product 1

HCID 4390393ST51003135

Conditions

Temperature
100 °C

Procedure

A solution containing 2.0 g of 4-benzoyl-3-methyl-1 -phenyl-2-pyrazolin-5-one (commercially available e.g. Aldrich 15,660-4) in 4 ml of phosphorus oxychloride was stirred under nitrogen at 100° C. for 30 min. The mixture was poured into 40 ml of saturated sodium hydrogen carbonate solution and extracted three times with 30 ml of dichloromethane. Combined extracts were dried over magnesium sulphate, filtered and evaporated to give 2.0 g of (5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-phenyl-methanone as a yellow oil which was used without further purification.

Workup

  1. extractionextracted three times with 30 ml of dichloromethane
  2. dry with materialCombined extracts were dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-f9b91fa219904cb7a96e70ba343e9211
Source dataset
uspto-grants-2007_02
Patent number
US07183296B2

Reaction notes

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