Acetyl chloride → Methyl 4-acetamido-3-iodobenzoate

HRID 591691Notes

Reaction equation

HRID 591691 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([I:11])[CH:5]=1.[C:13](Cl)(=[O:15])[CH3:14]>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:13](=[O:15])[CH3:14])=[C:6]([I:11])[CH:5]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 4104649Methyl 4-amino-3-iodobenzoate

Product 1

HCID 15304890Methyl 4-acetamido-3-iodobenzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 4-amino-3-iodo-benzoic acid methyl ester (11.1 g, 40.0 mmol) in anhydrous pyridine (80 mL) was added acetyl chloride (3.30 g, 42.0 mmol) at 0° C. under nitrogen. Stirring was continued at 0° C. for 30 minutes. The ice-bath was removed, and stirring continued at room temperature for 16 hours. Pyridine was evaporated under reduced pressure. The residue was taken in ethyl acetate (300 mL). The organic phase washed with 2 N aqueous HCl (200 mL), water (200 mL), brine (200 mL), and was dried over anhydrous Na2SO4. Removal of solvent gave 4-acetylamino-3-iodo-benzoic acid methyl ester as a white solid. Yield: 12.7 g (99%).

Workup

  1. customThe ice-bath was removed
  2. stirringstirring
  3. waitcontinued at room temperature for 16 hours
  4. customPyridine was evaporated under reduced pressure
  5. washThe organic phase washed with 2 N aqueous HCl (200 mL), water (200 mL), brine (200 mL)
  6. dry with materialwas dried over anhydrous Na2SO4
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-47d525c397804e53b339b9040737d2b4
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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