Acetyl chloride → N-(5-fluoro-2-phenoxyphenyl)acetamide

HRID 1930194Notes

Reaction equation

HRID 1930194 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([CH:8]=1)[NH2:7].[C:16](Cl)(=[O:18])[CH3:17]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([NH:7][C:16](=[O:18])[CH3:17])[CH:8]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 196271325-Fluoro-2-phenoxyaniline

Product 1

HCID 44126830N-(5-fluoro-2-phenoxyphenyl)acetamideYield 91.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-fluoro-2-phenoxyaniline 3 (5.14 g, 25 mmol) was dissolved in pyridine (15 mL) in a dry flask. At 0° C., acetyl chloride (2.3 mL, 33 mmol) was slowly added to the reaction, which was then refluxed for one hour, and subsequently, concentrated by vacuum. The residue was purified via column chromatography (silica gel) using CHCl3 as the eluent to give N-(5-fluoro-2-phenoxyphenyl)acetamide 4 as white solid (5.6 g, 90%): 1H-NMR (300 MHz, CDCl3) δ 8.29 (dd, J=10.5, 3.0 Hz, 1H), 7.74 (br s, 1H), 7.36 (t, J=7.5 Hz, 2H), 7.15 (t, J=7.5 Hz, 1H), 6.98 (d, J=7.5 Hz, 2H), 6.81 (2d, J=5.4, 5.1 Hz, 1H), 6.70 (2 dd, J1=J2=J3=J4=3 Hz, 1H), 2.17 (s, 3H). MS (GC) m/z 245(M., 100%)

Workup

  1. temperaturewas then refluxed for one hour
  2. concentrationsubsequently, concentrated by vacuum
  3. customThe residue was purified via column chromatography (silica gel)

Sources & evidence

ORD record
ord-db1067c7c6264186bca388b37a6d1ede
Source dataset
uspto-grants-2012_05
Patent number
US08188116B2

Reaction notes

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