Sodium Sulfate → 4-(1-Dimethylamino-2-propylimino)-2-pentanone

HRID 2241074Notes

Reaction equation

HRID 2241074 reaction equation
[C:1]([CH2:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[O-]S([O-])(=O)=O.[Na+].[Na+].[CH3:15][N:16]([CH3:21])[CH2:17][CH:18]([NH2:20])[CH3:19]>C1COCC1>[CH3:15][N:16]([CH3:21])[CH2:17][CH:18]([N:20]=[C:1]([CH3:2])[CH2:4][C:5](=[O:7])[CH3:6])[CH3:19]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 31261AcetylacetoneHCID 990272-Amino-1-dimethylaminopropane

Product 1

HCID 866305184-(1-Dimethylamino-2-propylimino)-2-pentanoneYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10 g (199.76 mmol) acetylacetone in THF at room temperature loaded with 20 g of Na2SO4 was added 24.49 g (239.71 mmol) 1-dimethylamino-2-propylamine. The slurry was stirred for 16 hours at room temperature and reaction deemed to be complete by GC/MS. All volatiles were evaporated off under vacuum and unreacted acetylacetone and diamine were removed by heating at 60° C. under 100 mTorr vacuum for 2 hours. Yellow residual oil was purified via vacuum transfer heating at 130° C. under 100 mTorr vacuum. 13.5 g of light yellow oil was obtained as pure product with a yield of 74%.

Workup

  1. customat room temperature
  2. customreaction
  3. customAll volatiles were evaporated off under vacuum and unreacted acetylacetone and diamine
  4. customwere removed
  5. temperatureby heating at 60° C. under 100 mTorr vacuum for 2 hours
  6. customYellow residual oil was purified via vacuum transfer
  7. temperatureheating at 130° C. under 100 mTorr vacuum

Sources & evidence

ORD record
ord-c3cc1b93a07e4cdb95ea2b20ffcca3db
Source dataset
uspto-grants-2010_05
Patent number
US07723493B2

Reaction notes

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