Allyl bromide → HCID 86749205, compound

HRID 375073Notes

Reaction equation

HRID 375073 reaction equation
[OH:1][C:2]1[C:6]2[CH:7]=[C:8]([N:11]3[C:20](=[O:21])[C:15]4[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=4[C:12]3=[O:13])[CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:28](Br)[CH:29]=[CH2:30]>CN(C)C=O.O>[CH2:30]([O:1][C:2]1[C:6]2[CH:7]=[C:8]([N:11]3[C:20](=[O:21])[C:15]4[CH2:16][CH2:17][CH2:18][CH2:19][C:14]=4[C:12]3=[O:13])[CH:9]=[CH:10][C:5]=2[O:4][N:3]=1)[CH:29]=[CH2:28]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 178514956HCID 178514956, compound

Product 1

HCID 86749205HCID 86749205, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(3-hydroxy-1,2-benzisoxazol-5-yl)-1-cyclohexene-1,2-dicarboximide (0.75 g, 2.64 mmol), potassium carbonate (0.6 g, 4.35 mmol) and allyl bromide (1 g, 8.3 mmol) in N,N-dimethylformamide is heated at 60°-70° C. for 2 hours and diluted with water. The aqueous mixture is extracted with ether. The organic extracts are combined, washed sequentially with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a yellow oil. Column chromatography of the oil using silica gel and ether/hexanes solutions yields a gum. A solution of the gum in an ether/hexanes mixture is passed through a plug of silica gel and crystallized to give the title product as a pale yellow solid, mp 88°-89° C.

Workup

  1. temperatureis heated at 60°-70° C. for 2 hours
  2. extractionThe aqueous mixture is extracted with ether
  3. washwashed sequentially with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a yellow oil
  7. customyields a gum
  8. customcrystallized

Sources & evidence

ORD record
ord-7ecb57be3abe4d369573eec4576c51f0
Source dataset
uspto-grants-1996_01
Patent number
US05484763

Reaction notes

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