Water → 1-(4-Bromo-2-thienyl)-2-(diallylamino)ethanone

HRID 1618975Notes

Reaction equation

HRID 1618975 reaction equation
Br[CH2:2][C:3]([C:5]1[S:6][CH:7]=[C:8]([Br:10])[CH:9]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:17]([NH:20][CH2:21][CH:22]=[CH2:23])[CH:18]=[CH2:19].O>C(#N)C>[Br:10][C:8]1[CH:9]=[C:5]([C:3](=[O:4])[CH2:2][N:20]([CH2:21][CH:22]=[CH2:23])[CH2:17][CH:18]=[CH2:19])[S:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 31279DiallylamineHCID 128903462-Bromo-1-(4-bromo-2-thienyl)ethanone

Product 1

HCID 866978881-(4-Bromo-2-thienyl)-2-(diallylamino)ethanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 1-(4-bromothiophen-2-yl)ethanone (10 g, 48.8 mmol) in methanol (98 mL) and dichloromethane (163 mL) is added tetra-n-butylammonium tribromide (28.8 g, 58.5 mmol). The reaction mixture is concentrated under reduced pressure at 50° C. to give a residue which is purified by silica gel chromatography, eluting with dichloromethane to give crude 2-bromo-1-(4-bromo-2-thienyl)ethanone. To a solution of the crude 2-bromo-1-(4-bromo-2-thienyl)ethanone in acetonitrile (200 ml) is added potassium carbonate (20.2 g, 146 mmol) and diallylamine (9.48 g, 97.5 mmol). The reaction is stirred at room temperature for 2 hours. Water is added and the solution is extracted with ethyl acetate. The organic phases are combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the crude title compound. ES/MS (m/e): (79Br/81Br) 300/302 (M+H).

Workup

  1. extractionthe solution is extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-558a88355e6f48a599c3c6ce8b03de79
Source dataset
uspto-grants-2014_07
Patent number
US08772282B2

Reaction notes

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