Sodium Chloride → 2-[Allyl(2,4-dimethoxybenzyl)amino]-1-(3-bromophenyl)ethanone

HRID 1693176Notes

Reaction equation

HRID 1693176 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](=[O:8])[CH2:6]Br.C(N(CC)C(C)C)(C)C.[CH2:21]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=1[O:34][CH3:35])[CH:22]=[CH2:23].C(=O)(O)[O-].[Na+].[Cl-].[Na+]>ClCCl.C(Cl)(Cl)Cl>[CH2:21]([N:24]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=1[O:34][CH3:35])[CH2:6][C:5]([C:4]1[CH:9]=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=1)=[O:8])[CH:22]=[CH2:23]

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5195852-Bromo-1-(3-bromophenyl)ethan-1-oneHCID 4722371HCID 4722371, compound

Product 1

HCID 578275522-[Allyl(2,4-dimethoxybenzyl)amino]-1-(3-bromophenyl)ethanoneYield 98.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

3-Bromophenacyl bromide (20.9 g) was dissolved in dichloromethane (400 mL). After ice-cooling the solution, N,N-diisopropylethylamine (14.3 mL) and allyl(2,4-dimethoxybenzyl)amine (18.7 g) were dissolved in dichloromethane (50 mL) and added dropwise. The reaction solution was gradually warmed to room temperature while dipping in an ice water bath, and stirred for about 20 hours. Chloroform, a saturated sodium bicarbonate solution and a saturated sodium chloride solution were sequentially added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate (2 g). The drying agent was removed by filtration and then the filtrate was concentrated under reduced pressure to obtain a crude product. The product was subjected to silica gel column chromatography to obtain the title compound (29.88 g).

Workup

  1. additionadded dropwise
  2. customwhile dipping in an ice water bath
  3. customthe organic layer was separated
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate (2 g)
  5. customThe drying agent was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customto obtain a crude product

Sources & evidence

ORD record
ord-3e9ccba624b946f08ec9c419ae7bd35f
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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