Phosphorus oxychloride → [5-chloro-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone

HRID 350869

Reaction equation

HRID 350869 reaction equation
O[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[N:5]=[C:4]([CH3:16])[C:3]=1[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18].C(=O)([O-])O.[Na+].P(Cl)(Cl)([Cl:32])=O>>[Cl:32][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[N:5]=[C:4]([CH3:16])[C:3]=1[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178490912HCID 178490912, compound

Product 1

HCID 22747458[5-chloro-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone

Conditions

Temperature
40 °C

Procedure

A solution containing 400 mg of [5-hydroxy-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone in 5 ml of phosphorus oxychloride was heated at 40° C. for 30 min. The mixture was poured into iced saturated sodium hydrogen carbonate and extracted with dichloromethane three times. The combined extracts were washed with brine then dried over anhydrous magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using diethyl ether/hexane (1:3) for the elution to give 170 mg of [5-chloro-1-(4-methoxybenzyl)-3-methyl -1H-pyrazol-4-yl]-phenyl-methanone as a yellow gum.

Workup

  1. extractionextracted with dichloromethane three times
  2. washThe combined extracts were washed with brine
  3. dry with materialthen dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel
  7. washfor the elution

Sources & evidence

ORD record
ord-867ff2ef71bf43239c783fd732edff86
Source dataset
uspto-grants-2007_02
Patent number
US07183296B2

Linked notes

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