Iodoethane → HCID 20360292, compound

HRID 2082714Notes

Reaction equation

HRID 2082714 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:7]([C:8]([NH2:10])=[O:9])[C:6]([OH:12])=[CH:5][CH:4]=1.I[CH2:14][CH3:15]>[Na].C(O)C>[CH2:14]([O:12][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][C:7]=1[C:8]([NH2:10])=[O:9])[CH3:15]

Participants

5

Reactant 2

HCID 6340IodoethaneHCID 119977Salicylamide, 5-methoxy-

Product 1

HCID 20360292HCID 20360292, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 5360545SodiumSolvent

Procedure

5-Methoxysalicylamide (41.8 g., 0.250 mole) was dissolved in a solution of sodium (6.37 g., 0.277 g-atom) in ethanol (250 ml.). To the resulting cooled (ice-water) solution was added iodoethane (38.9 g., 0.250 mole) over a period of 20 minutes. The reaction mixture was allowed to warm to room temperature over 0.75 hour and then was heated under reflux for 19 hours. The mixture was concentrated and the residue triturated with water. The mixture was filtered and the collected solid recrystallized from acetonitrile to give 2-ethoxy-5-methoxybenzamide (34.5 g., 70.7%), m.p. 128°-130°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 19 hours
  3. concentrationThe mixture was concentrated
  4. customthe residue triturated with water
  5. filtrationThe mixture was filtered
  6. customthe collected solid recrystallized from acetonitrile

Sources & evidence

ORD record
ord-ad69d442637b4842a45739cba7f6e3d0
Source dataset
uspto-grants-1978_04
Patent number
US04082751

Reaction notes

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