Iodoethane → HCID 86695311, compound

HRID 573513Notes

Reaction equation

HRID 573513 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([Cl:22])[CH:21]=1)[O:5][NH:6][C:7]([NH:9][C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:12])[CH3:11])=[O:8].C(=O)([O-])[O-].[K+].[K+].I[CH2:30][CH3:31].C(OCC)(=O)C>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([Cl:22])[CH:21]=1)[O:5][N:6]([CH2:30][CH3:31])[C:7]([NH:9][C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:12])[CH3:11])=[O:8]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 86695309HCID 86695309, compound

Product 1

HCID 86695311HCID 86695311, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.89 g of 1-(3-bromo-5-chlorophenoxy)-3-(2-phenylpropan-2-yl)urea was dissolved in 30 ml of N,N-dimethyl formamide. The resulting solution was added to a mixture of 5.18 g of potassium carbonate and 1.17 g of iodoethane, followd by stirring for one night at room temperature. Ethyl actate was then added to the susulting solution. The resulting mixture was washed with ammonium chloride, and the organic layer was dried with magnesium sulfate. After filtration, the solvent was distilled off. The resulting residues was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=5:1) to obtain the target compound of 1-(3-bromo-5-chlorophenoxy)-1-ethyl-3-(2-phenylpropan-2-yl)urea (2.86 g, yield: 92%).

Workup

  1. washThe resulting mixture was washed with ammonium chloride
  2. dry with materialthe organic layer was dried with magnesium sulfate
  3. filtrationAfter filtration
  4. distillationthe solvent was distilled off
  5. customThe resulting residues was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-14fcd12b95e547e1849a930e2f52cab0
Source dataset
uspto-grants-2015_05
Patent number
US09029601B2

Reaction notes

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