Sodium Iodide → 3-Hexyl-6-(3-nitrophenyl)-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carbonitrile

HRID 428971Notes

Reaction equation

HRID 428971 reaction equation
Cl[CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)[C:3]#[N:4].[CH2:14]([N:20]1[C:24](=[O:25])[CH:23]=[CH:22][C:21]1=[O:26])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.O>[CH2:14]([N:20]1[C:21](=[O:26])[CH:22]2[CH:23]([C:2]2([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=2)[C:3]#[N:4])[C:24]1=[O:25])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 4641341-Hexylpyrrole-2,5-dioneHCID 22141268HCID 22141268, compound

Product 1

HCID 221412573-Hexyl-6-(3-nitrophenyl)-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carbonitrileYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-chloro-2-(3-nitrophenyl)acetonitrile (Preparation 112, 103 mg, 0.524 mmol) and 1-hexyl-1H-pyrrole-2,5-dione (Preparation 56, 79 mg, 0.436 mmol) in N,N-dimethylformamide (2 ml) was added dropwise over 30 min to a stirred slurry of potassium carbonate (120 mg, 0.868 mmol) and sodium iodide (33 mg, 0.22 mmol) in N,N-dimethylformamide (4 ml) and water (0.1 ml) at 0° C. The reaction mixture was stirred for 30 min at 0° C. and then allowed to warm to room temperature. After stirring at room temperature for 2 h the mixture was diluted with water (10 ml) and extracted with ethyl acetate (3×5 ml). The combined organic phases were dried (MgSO4) and concentrated in vacuo to give a residue which was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (5:1 and then 3:1). This gave the title compound as brown needles (47 mg, 32%).

Workup

  1. temperatureto warm to room temperature
  2. stirringAfter stirring at room temperature for 2 h the mixture
  3. extractionextracted with ethyl acetate (3×5 ml)
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a residue which
  7. customwas purified by column chromatography on silica gel eluting with hexane:ethyl acetate (5:1

Sources & evidence

ORD record
ord-2b0af16d8d0048038da962ec20161963
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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