Ethyl formate → N-(2-Iodophenyl)formamide

HRID 266673Notes

Reaction equation

HRID 266673 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH:9](OCC)=[O:10].[H-].[Na+]>C1COCC1>[CH:9]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[I:1])=[O:10]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 119952-IodoanilineHCID 24758Sodium hydride

Product 1

HCID 10977764N-(2-Iodophenyl)formamideYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-iodaniline (6.0 g, 27.4 mmol) and ethyl formate (11.1 mL, 137.4 mmol) in 200 mL of THF was added dropwise to a suspension of sodium hydride (1.4 g, 34.2 mmol) in 250 mL of THF. The mixture was stirred at room temperature for 24 hours, quenched with water and extracted into ethyl acetate. The organic extract was dried (MgSO4), filtered and concentrated to give 6.3 g of crude N-formyl-2-iodoaniline as a tan solid.

Workup

  1. customquenched with water
  2. extractionextracted into ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c79512115f2642f28ebdd72bcd204469
Source dataset
uspto-grants-1997_07
Patent number
US05652237

Reaction notes

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