Acetyl chloride → 2'-Iodoacetanilide

HRID 2264691Notes

Reaction equation

HRID 2264691 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-7a6285ea60454575b278ea10a7186def
Source dataset
uspto-grants-2010_12
Patent number
US07855224B2

Reaction notes

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