4-Iodophenol → N,N-bis-(isopropyl)-2-(4-iodophenoxy)-acetamide

HRID 400245Notes

Reaction equation

HRID 400245 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH:11]([N:14]([CH:19]([CH3:21])[CH3:20])[C:15](=[O:18])[CH2:16]Br)([CH3:13])[CH3:12]>O1CCCC1>[CH:11]([N:14]([CH:19]([CH3:21])[CH3:20])[C:15](=[O:18])[CH2:16][O:10][C:7]1[CH:8]=[CH:9][C:4]([I:3])=[CH:5][CH:6]=1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 108944-IodophenolHCID 24758Sodium hydrideHCID 109001912-Bromo-N,N-diisopropylacetamide

Product 1

HCID 21841486N,N-bis-(isopropyl)-2-(4-iodophenoxy)-acetamideYield 108.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1.38 g of 50% sodium hydride suspended in oil were added under an inert gas atmosphere to a solution of 5.2 g of paraiodophenol in 30 ml of tetrahydrofuran and after stirring at 0° C., then 6.30 g of N,N-bis-(isopropyl)-2-bromo-acetamide (Preparation 8) were added. After stirring for 2 hours while allowing the temperature to rise to 20° C., the reaction medium was poured into ice-cooled water and filtration was carried out followed by drying to obtain 9.3 g of the expected product.

Workup

  1. stirringAfter stirring for 2 hours
  2. customto rise to 20° C.
  3. additionthe reaction medium was poured into ice-
  4. temperaturecooled
  5. filtrationwater and filtration
  6. customby drying

Sources & evidence

ORD record
ord-940f23f9855b404abc4f80ab5f81b82b
Source dataset
uspto-grants-1998_10
Patent number
US05827887

Reaction notes

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