N-bromobutanimide → HCID 57517513, compound

HRID 2368147Notes

Reaction equation

HRID 2368147 reaction equation
BrN1C(=[O:7])CCC1=O.[CH:9]1([CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([N+:22]([O-:24])=[O:23])[CH:16]=2)[CH2:11][CH2:10]1>C(OCC)(=O)C.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH:9]1([CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]=[O:7])=[C:17]([N+:22]([O-:24])=[O:23])[CH:16]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 57517511HCID 57517511, compound

Product 1

HCID 57517513HCID 57517513, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,2′-azobis(isobutyronitrile) (0.122 g), N-bromosuccinimide (3.19 g) and 4-(2-cyclopropylethoxy)-1-methyl-2-nitrobenzene (3.30 g) in ethyl acetate (100 mL) was refluxed for 8 hr. The reaction mixture was allowed to cool to room temperature, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The obtained solution was filtered with a short silica gel pad, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in acetonitrile (150 mL), and molecular sieves 4A (10 g) and 4-methylmorpholine N-oxide (2.02 g) were added thereto at 0° C. The reaction mixture was stirred under a nitrogen atmosphere at room temperature for 3 hr, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (1.90 g).

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe obtained solution was filtered with a short silica gel pad
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe obtained residue was dissolved in acetonitrile (150 mL)
  6. additionmolecular sieves 4A (10 g) and 4-methylmorpholine N-oxide (2.02 g) were added
  7. customat 0° C
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-21b97ad99f1f40699f273e26a6b2a311
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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