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

HRID 47629

Reaction equation

HRID 47629 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-bbcc7bc887b045c394ac64c27e654894
Source dataset
uspto-grants-2004_03
Patent number
US06699887B2

Linked notes

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