N-Ethyl-2-iodobenzamide → HCID 18630027, compound

HRID 1060147Notes

Reaction equation

HRID 1060147 reaction equation
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].[CH2:7]([NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1I)[CH3:8]>N1C=CC=CC=1.[OH-].[NH4+]>[CH2:7]([NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:4][C:2]([CH3:5])([CH3:3])[CH3:1])[CH3:8]

Participants

5

Reactant 2

HCID 967640N-Ethyl-2-iodobenzamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 18630027HCID 18630027, compoundYield 29.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 14923Ammonium HydroxideSolvent

Procedure

Potassium t-butoxide (12.25 g, 0.109 mol) was dissolved in pyridine (50 mL) and cuprous chloride (10.81 g, 0.109 mol) was added. The black suspension was stirred at RT for 30 min and N-ethyl-2-iodobenzamide (10.00 g, 36.4 mmol) dissolved in pyridine (20 mL) was added dropwise. The mixture was stirred at room temperature for 1 h and was poured in aq ammonium hydroxide and extracted with ether. The organic extracts were washed with 1 N NaOH, brine, dried (MgSO4) and concentrated to afford a brown semi-solid. The crude product was purified by flash chromatography (ethyl acetate/hexanes) to afford the title compound as a light yellow solid (2.36 g, 29%). m.p. 34.5-36° C.

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred at room temperature for 1 h
  3. extractionextracted with ether
  4. washThe organic extracts were washed with 1 N NaOH, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto afford a brown semi-solid
  8. customThe crude product was purified by flash chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-fdc52f37f474474bb8c84db39602cc3d
Source dataset
uspto-grants-2003_02
Patent number
US06521603B2

Reaction notes

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