Benzyl Bromide → HCID 15136695, compound

HRID 1614337Notes

Reaction equation

HRID 1614337 reaction equation
[CH3:1][C:2]1([CH3:8])[CH2:6][NH:5][NH:4][C:3]1=[O:7].[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])(O)=O.[Na+]>C(O)C.C(OCC)C>[CH2:9]([N:5]1[CH2:6][C:2]([CH3:8])([CH3:1])[C:3](=[O:7])[NH:4]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 12563150HCID 12563150, compound

Product 1

HCID 15136695HCID 15136695, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

4,4-dimethyl-3-pyrazolidinone [1.42 g] and benzyl bromide [1.78 mL] and NaHCO3 [1.26 g] were combined in 5 mL ethanol. The mixture was heated at reflux for 30 minutes. The reaction mixture was cooled to room temperature, diluted with diethyl ether (50 mL), dried with MgSO4, filtered and evaporated. The resulting oil was chromatographed on silica gel to yield 1.22 g (52%) of 1-Benzyl-4,4-dimethyl-3-pyrazolidinone as a light oil. 1H NMR: 7.6-7.2 (5H, m), 3.8-3.4 (4H, m), 1.2 (6H, s).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 30 minutes
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-5f71700c202a4424bdcec368a767730b
Source dataset
uspto-grants-1993_03
Patent number
US05196546

Reaction notes

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