Iodoacetamide → HCID 58387824, compound

HRID 2381050Notes

Reaction equation

HRID 2381050 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([OH:10])[C:7]=1[CH:8]=[O:9].[H-].[Na+].I[CH2:14][C:15]([NH2:17])=[O:16]>CN(C=O)C>[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([CH:5]=[CH:4][CH:3]=1)[O:10][CH2:14][C:15]([NH2:17])=[O:16]

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 24758Sodium hydrideHCID 5283932-Chloro-6-hydroxybenzaldehyde

Product 1

HCID 58387824HCID 58387824, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.1 1.0 g of 6-chlorosalicylaldehyde 9 is dissolved in 30 ml of DMF, 0.26 g of NaH (60% suspension in paraffin oil) is carefully added with cooling, and the mixture is stirred at RT for 45 min. 1.30 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 1.28 g (90%) of 2-(3-chloro-2-formylphenoxy)acetamide 10; MS-EI (M+)=213.

Workup

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

Sources & evidence

ORD record
ord-10faed9f46f64a9ca51a767de27bbac0
Source dataset
uspto-grants-2012_09
Patent number
US08258151B2

Reaction notes

Loading…