Acetyl chloride → 2'-Iodoacetanilide

HRID 491027Notes

Reaction equation

HRID 491027 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:9](Cl)(=[O:11])[CH3:10]>N1C=CC=CC=1.Cl>[I:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:9](=[O:11])[CH3:10]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 119952-Iodoaniline

Product 1

HCID 1405592'-Iodoacetanilide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

2-Iodoaniline (1.00 g, 4.56 mmol) was dissolved in pyridine (5 mL) and cooled to 0° C. After acetyl chloride (314 μL, 5.94 mmol) was added, the reaction was stirred at 0° C. for 1 hour and then at room temperature for 2 hours. The reaction was diluted with 1 N HCl and extracted with ether. The organic layer was dried (MgSO4) and concentrated to give the desired acetamide (assumed quantitative), which was used in the next reaction without further purification.

Workup

  1. waitat room temperature for 2 hours
  2. extractionextracted with ether
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b315f9eac74f422d83fa6252ec00be08
Source dataset
uspto-grants-2009_05
Patent number
US07528262B2

Reaction notes

Loading…