Iodoethane → HCID 20360292, compound

HRID 437421Notes

Reaction equation

HRID 437421 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 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. customcollected solid
  7. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-fc8ac2d5c136432e85d91d2bb8876718
Source dataset
uspto-grants-1977_06
Patent number
US04031093

Reaction notes

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