Allyl bromide → 1-(4-Acetylaminophenyl)-3-allyl-3-azabicyclo[3.1.0]hexane-2,4-dione

HRID 1904798Notes

Reaction equation

HRID 1904798 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]23[CH2:16][CH:15]2[C:14](=[O:17])[NH:13][C:12]3=[O:18])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[H-].[Na+].[CH2:21](Br)[CH:22]=[CH2:23]>CN(C)C=O>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]23[CH2:16][CH:15]2[C:14](=[O:17])[N:13]([CH2:23][CH:22]=[CH2:21])[C:12]3=[O:18])=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 140689461-(4-Acetylaminophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

Product 1

HCID 140689471-(4-Acetylaminophenyl)-3-allyl-3-azabicyclo[3.1.0]hexane-2,4-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.2 g of 1-(4-acetylaminophenyl)-3-azabicyclo[3.1.0]hexane-2,4dione are dissolved in 25 ml of dimethylformamide and to this solution are added 180 mg of sodium hydride under nitrogen. The mixture is stirred for 1 hour at room temperature. The clear, pale yellow solution is cooled in an ice-water bath and then a solution of 0.65 ml of allyl bromide in 5 ml of dimethylformamide is added dropwise. The reaction mixture is stirred overnight and then the solvent is stripped off. The residue is partitioned twice between ethyl acetate and water. The organic phases are dried over magnesium sulfate, filtered and concentrated, and the residue is crystallised from ethyl acetate/ether/petroleum ether. The title compound is obtained in the form of white crystals with a melting melting point of 113°-116° C. and with Rf=0.33 on thin-layer silica gel plates in the system methylene chloride/methanol (10:1).

Workup

  1. temperatureThe clear, pale yellow solution is cooled in an ice-water bath
  2. stirringThe reaction mixture is stirred overnight
  3. customThe residue is partitioned twice between ethyl acetate and water
  4. dry with materialThe organic phases are dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue is crystallised from ethyl acetate/ether/petroleum ether

Sources & evidence

ORD record
ord-a822a2374ef1434994057c032e39e7ff
Source dataset
uspto-grants-1989_06
Patent number
US04839379

Reaction notes

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