Acetyl chloride → 2-Iodo-N-phenylacetamide

HRID 1452731Notes

Reaction equation

HRID 1452731 reaction equation
[C:1](Cl)(=O)[CH3:2].[I:5][C:6]1C=CC=C[C:7]=1[NH2:8].[OH-:13].[Na+].[CH2:15]1[CH2:19]O[CH2:17][CH2:16]1.O>O>[I:5][CH2:6][C:7]([NH:8][C:15]1[CH:16]=[CH:17][CH:2]=[CH:1][CH:19]=1)=[O:13]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 119952-IodoanilineHCID 14798Sodium HydroxideHCID 21881883Oxolane--water (1/1)

Product 1

HCID 112077032-Iodo-N-phenylacetamideYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Acetyl chloride (6 mmol) was added dropwise to the mixture of 2-iodoaniline (5 mmol) and sodium hydroxide (13 mmol) in THF/H2O (1/1, 4 mL). Stirred the mixture at 0° C. for 2 h, and then at room temperature for overnight. The mixture was diluted with 10 mL water and extracted with diethyl ether 3 times. The combined organic layer was washed with water 3 times and brine. Dried over sodium sulfate, filtered, and removed solvent. The residue was then purified by column chromatography afforded white solid of 2-iodoacetanilide 68% yield. NMR

Workup

  1. waitat room temperature for overnight
  2. extractionextracted with diethyl ether 3 times
  3. washThe combined organic layer was washed with water 3 times and brine
  4. dry with materialDried over sodium sulfate
  5. filtrationfiltered
  6. customremoved solvent
  7. customThe residue was then purified by column chromatography

Sources & evidence

ORD record
ord-0f16092661174a27849d310ccea1fe7e
Source dataset
uspto-grants-2009_01
Patent number
US07473786B1

Reaction notes

Loading…