Allyl bromide → HCID 23117635, compound

HRID 1178322Notes

Reaction equation

HRID 1178322 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH:5]([N:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1)[CH3:2].[OH-].[Na+].[CH2:25](Br)[CH:26]=[CH2:27].S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[CH:15](=[N:14][C:5]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1)([CH2:27][CH:26]=[CH2:25])[C:4]([O:3][CH2:1][CH3:2])=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 11433187Bis(tetrabutylammonium) sulphateHCID 58696280HCID 58696280, compound

Product 1

HCID 23117635HCID 23117635, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl(benzylidene-amino)-(3,4-dichlorophenyl)acetate (425 g) was dissolved in methylene chloride (1.8 L). 10N Aqueous sodium hydroxide (1.2 L), allyl bromide (158 mL), and tetrabutylammonium sulfate (41 g) were added to the resultant solution, followed by stirring at room temperature for one hour. The reaction mixture was subjected to partitioning. Water (1 L) was added to the aqueous layer, and then the mixture was extracted with methylene chloride. The thus-obtained organic layer was washed with saturated brine, dried over sodium sulfate anhydrate, and concentrated under reduced pressure, to thereby give the title compound (518 g). The title compound was used in the next step without further purification.

Workup

  1. customto partitioning
  2. additionWater (1 L) was added to the aqueous layer
  3. extractionthe mixture was extracted with methylene chloride
  4. washThe thus-obtained organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate anhydrate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1c53244836ad429c81e46983e8c7443d
Source dataset
uspto-grants-2007_10
Patent number
US07276511B2

Reaction notes

Loading…