Benzoylacetone → 2-diazo-1-phenyl-1,3-butanedione

HRID 1292331Notes

Reaction equation

HRID 1292331 reaction equation
[N-]=[N+:2]=[N-:3].[Na+].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[C:16]([CH2:24][C:25]([CH3:27])=[O:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>O.C(O)C>[N+:2](=[C:24]([C:25](=[O:26])[CH3:27])[C:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:23])=[N-:3]

Participants

7

Reactant 4

HCID 7166BenzoylacetoneHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 33557Sodium Azide

Product 1

HCID 5693592-diazo-1-phenyl-1,3-butanedioneYield 52.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of sodium azide (683 mg, 10.5 mmol), p-toluenesulfonyl chloride (2.0 grams, 10.5 mmol), and 70% aqueous ethanol (30 mL) was stirred at room temperature for 1 hour. 1-Benzoylacetone (1.62 grains, 10.0 mmol) and triethylamine (1.46 mL, 10.5 mmol) were added. The reaction mixture was stirred at room temperature for 3 hours and then poured into deionized water (200 mL). The mixture was extracted with petroleum ether (2×200 mL). The extracts were combined and then washed with a saturated aqueous sodium chloride solution. The organic solution was dried using anhydrous magnesium sulfate, filtered, and concentrated to give 0.980 grams of 2-diazo-1-phenyl-1,3-butanedione as a yellow oil. Decomposition temperature: 128° C. (by DSC).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hours
  2. extractionThe mixture was extracted with petroleum ether (2×200 mL)
  3. washwashed with a saturated aqueous sodium chloride solution
  4. customThe organic solution was dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c40f0a175047466a82ad69919567ff86
Source dataset
uspto-grants-1998_05
Patent number
US05756689

Reaction notes

Loading…