Water → N-ethyl-4-iodobenzamide

HRID 840477Notes

Reaction equation

HRID 840477 reaction equation
[CH2:1]([NH2:3])[CH3:2].[I:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1.O>C1COCC1.ClCCl>[CH2:1]([NH:3][C:9](=[O:10])[C:8]1[CH:12]=[CH:13][C:5]([I:4])=[CH:6][CH:7]=1)[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 6341EthylamineHCID 743734-Iodobenzoyl chloride

Product 1

HCID 875746N-ethyl-4-iodobenzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

90 ml (45 mmol) of a 0.5N solution of ethylamine in THF were introduced into a round-bottomed flask and a solution of 4 g (15 mmol) of 4-iodobenzoyl chloride in 20 ml of dichloromethane was added dropwise. Stirring was carried out at room temperature for one hour and the reaction mixture was poured into water and extracted with ethyl ether. The organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with dichloromethane. After evaporating the solvents, 3.41 g (82%) of the expected amide was recovered.

Workup

  1. extractionextracted with ethyl ether
  2. customThe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customwas purified by chromatography on a silica column
  7. washeluted with dichloromethane
  8. customAfter evaporating the solvents, 3.41 g (82%) of the expected amide
  9. customwas recovered

Sources & evidence

ORD record
ord-5d312df8cad84afc9ee6d19727c9e90c
Source dataset
uspto-grants-2002_04
Patent number
US06368608B1

Reaction notes

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