Water → 2-Propenamide, 3-phenyl-

HRID 1181607Notes

Reaction equation

HRID 1181607 reaction equation
C([N:3]([CH2:6][CH3:7])CC)C.C(Cl)/C=[CH:10]/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH2:18]>ClCCl>[C:6]([NH2:3])(=[O:18])[CH:7]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 639658Cinnamyl chloride

Product 1

HCID 121352-Propenamide, 3-phenyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a dichloromethane solution of a poly(propyleneimine)dendrimer (1.0 g, 3.2 mmol, made by Aldrich Corporation) of the first generation (n=1 in FIG. 8) containing a catalytic quantity of triethylamine, a solution of trans-cinnamyl chloride (0.63 g, 3.7 mmol, made by Aldrich Corporation) was dropped, and the resultant solution was stirred at 0° C. for one hour and then at room temperature for 40 hours. This reaction liquid was diluted with dichloromethane, was cleaned sequentially with ion-exchange water, an aqueous solution of sodium carbonate and an aqueous solution of sodium chloride, and was dried with magnesium sulfate. After filtration, dichloromethane was removed by an evaporator. The crude product was dialyzed and reprecipitated repetitively for three times, and was dried under a reduced pressure. Then, a white solid was obtained.

Workup

  1. customThis reaction liquid
  2. dry with materialan aqueous solution of sodium carbonate and an aqueous solution of sodium chloride, and was dried with magnesium sulfate
  3. filtrationAfter filtration, dichloromethane
  4. customwas removed by an evaporator
  5. customThe crude product was dialyzed
  6. customreprecipitated repetitively for three times
  7. customwas dried under a reduced pressure
  8. customThen, a white solid was obtained

Sources & evidence

ORD record
ord-62de3d9085d4447b9f1d73c9c38c1c88
Source dataset
uspto-grants-2007_10
Patent number
US07285604B2

Reaction notes

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