Potassium Carbonate → 2-(3-Cyanophenoxy)acetamide

HRID 56300Notes

Reaction equation

HRID 56300 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].Br[CH2:11][C:12]([NH2:14])=[O:13].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:5]([C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][CH2:11][C:12]([NH2:14])=[O:13])#[N:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 696322-Bromoacetamide

Product 1

HCID 246951822-(3-Cyanophenoxy)acetamideYield 28.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 3-hydroxybenzonitrile (2.38 g, 20.0 mmol), 2-bromoacetamide (3.04 g, 22.0 mmol) and K2CO3 (5.53 g, 40.0 mmol) in acetone (30 mL) was stirred at 75° C. overnight. It was then cooled to rt and filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a white solid (1.00 g, 28%).

Workup

  1. temperatureIt was then cooled to rt
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Sources & evidence

ORD record
ord-f6a10fb78cd94f29858478126bc5890d
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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