Iodoethane → 5-Chloro-2-ethoxybenzamide

HRID 437423

Reaction equation

HRID 437423 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([NH2:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.I[CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:13][CH3:14])=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 3480945-Chloro-2-hydroxybenzamide

Product 1

HCID 203602935-Chloro-2-ethoxybenzamideYield 36.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-chlorosalicylamide (16.0 g., 0.093 mole), iodoethane (31.8 g., 0.204 mole), and potassium carbonate (13.1 g., 0.095 mole) in ethanol (225 ml.) was heated under reflux for 20 hours. The hot mixture was filtered. The filtrate was reduced to dryness. The residue was triturated with water. The mixture was filtered and the collected solid recrystallized from acetonitrile to give 5-chloro-2-ethoxybenzamide (6.8 g., 36.6%) m.p. 136°-139°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hours
  3. filtrationThe hot mixture was filtered
  4. customThe residue was triturated with water
  5. filtrationThe mixture was filtered
  6. customthe collected solid recrystallized from acetonitrile

Sources & evidence

ORD record
ord-a41ab30757f346f09213a2bfca4b3c19
Source dataset
uspto-grants-1977_06
Patent number
US04031093

Linked notes

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