Iodoacetamide → 2-(2-Formyl-3-methoxyphenoxy)acetamide

HRID 2381047Notes

Reaction equation

HRID 2381047 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH:4]=[O:5].[H-].[Na+].I[CH2:15][C:16]([NH2:18])=[O:17]>CN(C=O)C>[CH:4]([C:3]1[C:6]([O:10][CH3:11])=[CH:7][CH:8]=[CH:9][C:2]=1[O:1][CH2:15][C:16]([NH2:18])=[O:17])=[O:5]

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 24758Sodium hydrideHCID 696926-Methoxysalicylaldehyde

Product 1

HCID 426046142-(2-Formyl-3-methoxyphenoxy)acetamideYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.1 1.0 g (6.57 mmol) of 2-hydroxy-6-methoxybenzaldehyde 1 is dissolved in 30 ml of DMF, 0.29 g of NaH (60% suspension in paraffin oil) is carefully added with cooling, and the mixture is stirred at RT for 45 min. 1.34 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 0.81 g (59%) of 2-(2-formyl-3-methoxyphenoxy)acetamide 3 as solid. MS-EI (M+)=209.

Workup

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

Sources & evidence

ORD record
ord-f8f1cb614c294f52ab4d0473517bd26e
Source dataset
uspto-grants-2012_09
Patent number
US08258151B2

Reaction notes

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