Iodoacetamide → 2-(2,3-Dimethylphenoxy)acetamide

HRID 2381048Notes

Reaction equation

HRID 2381048 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[H-].[Na+].I[CH2:13][C:14]([NH2:16])=[O:15]>CN(C=O)C>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH2:13][C:14]([NH2:16])=[O:15]

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 106872,3-DimethylphenolHCID 24758Sodium hydride

Product 1

HCID 159430302-(2,3-Dimethylphenoxy)acetamideYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.1 19.95 g of 2,3-dimethylphenol 6 are dissolved in 250 ml of DMF, 6.4 g of NaH (60% suspension in paraffin oil) are carefully added with cooling, and the mixture is stirred at RT for 45 min. 31.4 g of 2-iodoacetamide 2 are then added, and the reaction mixture is stirred overnight. The mixture is subsequently subjected to conventional work-up, giving 23.8 g (83%) of 2-(2,3-dimethylphenoxy)acetamide 7; MS-EI (M+)=179.

Workup

  1. temperaturewith cooling
  2. stirringthe reaction mixture is stirred overnight

Sources & evidence

ORD record
ord-292bf1039a6b46e199e39c8a0487328d
Source dataset
uspto-grants-2012_09
Patent number
US08258151B2

Reaction notes

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