Acetone → HCID 21536645, compound

HRID 1076445Notes

Reaction equation

HRID 1076445 reaction equation
[Br:1][C:2]1[C:3]([CH3:8])=[N:4][NH:5][C:6]=1[Br:7].CC(C)=O.C(=O)([O-])[O-].[K+].[K+].Br[CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>CCCCCC>[Br:7][C:6]1[C:2]([Br:1])=[C:3]([CH3:8])[N:4]([CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:5]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 178434484HCID 178434484, compound

Product 1

HCID 21536645HCID 21536645, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A reaction mixture consisting of a solution of 13.7 g. (0.057 mole) 4,5 -dibromo-3-methylpyrazole in 200 ml. acetone and 15.7 g. (0.114 mole) anhydrous potassium carbonate was heated at the reflux temperature with continuous stirring for 15 minutes. After cooling, 10.4 g. (0.06 mole) ethyl 2-bromopropionate was added. This reaction mixture was then heated at the reflux temperature for 2.5 hours. It was cooled and filtered. The acetone was then removed by evaporation under reduced pressure, and the residue thus obtained was dissolved in hot hexane. After chilling in a refrigerator the crystals that had formed were collected on a filter. There was thus obtained 14.5 g. (75% yield) of ethyl 3,4 -dibromo-α, 5-dimethylpyrazole-1-acetate having a melting point at 61° to 62° C.

Workup

  1. temperatureAfter cooling
  2. temperatureThis reaction mixture was then heated at the reflux temperature for 2.5 hours
  3. temperatureIt was cooled
  4. filtrationfiltered
  5. customThe acetone was then removed by evaporation under reduced pressure
  6. customthe residue thus obtained
  7. temperatureAfter chilling in a refrigerator the crystals that
  8. customhad formed
  9. customwere collected on a filter

Sources & evidence

ORD record
ord-d61ce0befc9348c9aa69e373cc1211b2
Source dataset
uspto-grants-1976_05
Patent number
US03957480

Reaction notes

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