Acetyl chloride → N-(4-Acetyl-3-fluoro-5-methylphenyl)acetamide

HRID 1465580Notes

Reaction equation

HRID 1465580 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:13](Cl)(=[O:15])[CH3:14].[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[C:13]([C:7]1[C:6]([CH3:8])=[CH:5][C:4]([NH:9][C:10](=[O:12])[CH3:11])=[CH:3][C:2]=1[F:1])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 59921881N-(3-fluoro-5-methylphenyl)acetamide

Product 1

HCID 86690882N-(4-Acetyl-3-fluoro-5-methylphenyl)acetamideYield 97.7%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

A dry CS2 solution (42 mL) containing N-(3-fluoro-5-methylphenyl)acetamide (30-1, 5.00 g, 29.9 mmol) and acetyl chloride (3.2 mL, 45 mmol) was slowly added with aluminum chloride (10 g, 74.8 mmol). The reaction mixture was heated at reflux for 2.0 h. The solution was cooled to room temperature and CS2 was decanted. The remaining syrup was poured into icy HCl, and the resultant solids were collected, re-dissolved in EtOH, and decolorized by charcoal. The solution was filtered and the filtrate was concentrated under vacuum to give N-(4-acetyl-3-fluoro-5-methyl-phenyl)acetamide (30-2, 6.10 g, 29.2 mmol) as light yellow solids in 97% yield: 1H NMR (500 MHz, CDCl3) δ 7.46 (d, J=12.4 Hz, 1 H), 6.93 (s, 1 H), 2.53 (d, J=3.8 Hz, 3 H), 2.31 (s, 3 H), 2.18 (s, 3 H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2.0 h
  3. customCS2 was decanted
  4. additionThe remaining syrup was poured into icy HCl
  5. customthe resultant solids were collected
  6. dissolutionre-dissolved in EtOH
  7. filtrationThe solution was filtered
  8. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-eb13e9056c5741dc96461ed2f2747d51
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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