Phosphorus oxychloride → ST51003135

HRID 47602Notes

Reaction equation

HRID 47602 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-21d2bfee8edd4fdebd8f25d5fc6d26d2
Source dataset
uspto-grants-2004_03
Patent number
US06699887B2

Reaction notes

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