Acetyl chloride → 2'-Iodoacetanilide

HRID 1092412Notes

Reaction equation

HRID 1092412 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-57a8314e94374a3bac43794109d4db44
Source dataset
uspto-grants-2012_03
Patent number
US08129424B2

Reaction notes

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