Water → 2-Azido-2-(4-isopropyl-2-methoxyphenyl)-4-nitro-2H-inden-1,3-dione

HRID 527128Notes

Reaction equation

HRID 527128 reaction equation
Cl[C:2]1([C:16]2[CH:21]=[CH:20][C:19]([CH:22]([CH3:24])[CH3:23])=[CH:18][C:17]=2[O:25][CH3:26])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N+:12]([O-:14])=[O:13])[C:3]1=[O:15].[N-:27]=[N+:28]=[N-:29].[Na+].[I-].[Na+].O>CC(C)=O>[N:27]([C:2]1([C:16]2[CH:21]=[CH:20][C:19]([CH:22]([CH3:24])[CH3:23])=[CH:18][C:17]=2[O:25][CH3:26])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N+:12]([O-:14])=[O:13])[C:3]1=[O:15])=[N+:28]=[N-:29]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 33557Sodium AzideHCID 714769712-Chloro-2-(4-isopropyl-2-methoxyphenyl)-4-nitro-2H-inden-1,3-dione

Product 1

HCID 714769722-Azido-2-(4-isopropyl-2-methoxyphenyl)-4-nitro-2H-inden-1,3-dioneYield 49.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-chloro-2-(4-isopropyl-2-methoxyphenyl)-4-nitro-2H-inden-1,3-dione (1.23 g, 3.2 mmol) was completely dissolved in acetone (30 ml). This solution was added with sodium azide (0.47 g, 7.2 mmol), sodium iodide (0.59 g, 3.9 mmol), water (6 ml), followed by heating 12 hrs under reflux. The reaction mixture was concentrated, and extracted with ethylacetate, and the concentrated organic layer was purified using column chromatography (ethylacetate:hexane=1:4) to afford the title compound (Brown syrup, 600 mg, 48%).

Workup

  1. temperatureby heating 12 hrs
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated
  4. extractionextracted with ethylacetate
  5. customthe concentrated organic layer was purified

Sources & evidence

ORD record
ord-af45f36cd8554334bdf61c1e4aef49b1
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

Loading…