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

HRID 350877Notes

Reaction equation

HRID 350877 reaction equation
[CH2:1]([N:3]1[C:7](O)=[C:6]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[C:5]([CH3:17])=[N:4]1)[CH3:2].C(=O)([O-])O.[Na+].P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:7]1[N:3]([CH2:1][CH3:2])[N:4]=[C:5]([CH3:17])[C:6]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178463090HCID 178463090, compound

Product 1

HCID 22747496(5-chloro-1-ethyl-3-methyl-1H-pyrazol-4-yl)-phenyl-methanone

Procedure

A solution of 2.6 g of (1-ethyl-5-hydroxy-3-methyl-1H-pyrazol-4-yl)-phenyl-methanone in 4 ml of phosphorus oxychloride was stirred at 80° C. for 1.5 h. The mixture was poured into 300 ml of saturated sodium hydrogen carbonate and extracted three times with 70 ml of dichloromethane. The combined extracts were dried over magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using ethyl acetate/petroleum ether (bp 40–60° C.) (1:4) for the elution to give 1.74 g of (5-chloro-1-ethyl-3-methyl-1H-pyrazol-4-yl)-phenyl-methanone as a pale yellow liquid. Mass spectrum (ES) m/z 249 [M+H]+, 290 [M+H+CH3CN]+.

Workup

  1. extractionextracted three times with 70 ml of dichloromethane
  2. dry with materialThe combined extracts were dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-2f1916c816904e9aa9442d39f47ec935
Source dataset
uspto-grants-2007_02
Patent number
US07183296B2

Reaction notes

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