Dimethylformamide → 5-Chloro-1-ethyl-3-methyl-1H-pyrazole-4-carbaldehyde

HRID 350886Notes

Reaction equation

HRID 350886 reaction equation
CN(C)[CH:3]=[O:4].P(Cl)(Cl)([Cl:8])=O.[CH2:11]([N:13]1[C:17](O)=[CH:16][C:15]([CH3:19])=[N:14]1)[CH3:12]>O>[Cl:8][C:17]1[N:13]([CH2:11][CH3:12])[N:14]=[C:15]([CH3:19])[C:16]=1[CH:3]=[O:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 178463089HCID 178463089, compound

Product 1

HCID 227475065-Chloro-1-ethyl-3-methyl-1H-pyrazole-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To 28.7 ml of anhydrous N,N-dimethylformamide at 0° C. were added slowly 80.7 ml of phosphorus oxychloride then 15.6 g of 2-ethyl-5-methyl-2H-pyrazol-3-ol. The mixture was stirred under nitrogen at 80° C. for 1 hour, poured into 700 ml of water at 0° C. then extracted six times with 350 ml of diethyl ether. The combined extracts were dried over magnesium sulphate, filtered and evaporated to leave 9.3 g of 5-chloro-1-ethyl-3-methyl-1H-pyrazole-4-carbaldehyde as an orange liquid which was used without further purification.

Workup

  1. extractionthen extracted six times with 350 ml of diethyl ether
  2. dry with materialThe combined extracts were dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-27a30c14765744a59db4f937d40e7352
Source dataset
uspto-grants-2007_02
Patent number
US07183296B2

Reaction notes

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